CN115246775A - Preparation method of N, N-dialkyl chlorinated fat and hydrochloride thereof - Google Patents
Preparation method of N, N-dialkyl chlorinated fat and hydrochloride thereof Download PDFInfo
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- CN115246775A CN115246775A CN202210994807.6A CN202210994807A CN115246775A CN 115246775 A CN115246775 A CN 115246775A CN 202210994807 A CN202210994807 A CN 202210994807A CN 115246775 A CN115246775 A CN 115246775A
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- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/74—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton by halogenation, hydrohalogenation, dehalogenation, or dehydrohalogenation
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Abstract
The invention discloses a preparation method of N, N-dialkyl chlorinated aliphatic amine and hydrochloride thereof, which comprises the following steps: (1) Dripping N, N-dimethyl propane diamine or N, N-dimethyl butane diamine into precooled hydrochloric acid solution, heating to 5-50 ℃, and dripping sodium nitrite solution for reaction; (2) And (2) after the reaction in the step (1) is finished, adjusting the pH value of the reaction liquid to 10-14, and standing and separating liquid to obtain the N, N-dialkyl chlorinated aliphatic amine. The invention takes cheap substituted diamine as raw material, in the presence of sodium nitrite and hydrochloric acid, N-dialkyl chlorinated aliphatic amine can be prepared by one step, and is mixed with hydrochloric acid solution for further distillation treatment to prepare N, N-dialkyl chlorinated aliphatic amine hydrochloride with more stable physicochemical property, which is convenient for storage. The method has the advantages of simple preparation process, cheap and easily obtained raw materials, low cost and high yield, and is suitable for industrial mass production, and the by-product is only sodium chloride.
Description
Technical Field
The invention relates to the technical field of organic chemical synthesis, in particular to a preparation method of N, N-dialkyl chlorinated aliphatic amine and hydrochloride thereof.
Background
N, N-dialkyl chloro fatty amine is an important intermediate for preparing fluorescent dye or medicine, for example, 3-chloro-N, N-dimethyl-1-propylamine is an intermediate for synthesizing bencyclane, benzydamine, tylden, chlorpromazine, trifluoropromazine, imipramine, amitriptyline, doxepin and other medicines. The N, N-dialkyl chlorinated aliphatic amine compound is unstable in property, difficult to store, usually converted into corresponding hydrochloride, and convenient to transport and store.
At present, the preparation methods of the N, N-dialkyl chlorinated aliphatic amine compounds mainly comprise the following two methods: (1) Taking corresponding alcohol as a reaction raw material, and carrying out substitution reaction with thionyl chloride or phosphorus oxychloride to prepare corresponding N, N-dialkyl chlorinated aliphatic amine; the thionyl chloride or phosphorus oxychloride used in the method has corrosivity and the industrial production safety is low. (2) Preparing corresponding N, N-dialkyl chlorinated fatty amine by using corresponding disubstituted amine and corresponding bromo-or iodo-alkyl chloride as reaction raw materials through an affinity substitution reaction; this method is improved in safety as compared with the method (1), and is also a method generally used at present. However, the two methods have the problems of high raw material price and higher cost for preparing the corresponding N, N-dialkyl chlorinated aliphatic amine. Taking the preparation of 3-chloro-N, N-dimethyl-1-propylamine as an example, the reaction raw materials prepared by the method (1) are 3-dimethylamino-1-propanol and thionyl chloride, wherein the price of the 3-dimethylamino-1-propanol is up to 225.9 yuan/mol, and the price of the main raw material is up to 230.5 yuan per 1mol of the product produced in 98 percent yield. If disubstituted amine and 1-bromo-3-chloropropane are adopted to prepare 3-chloro-N, N-dimethyl-1-propylamine, wherein the price of the 1-bromo-3-chloropropane is expensive and is about 61.7 yuan/mol, and the price of the main raw material 1-bromo-3-chloropropane reaches 71.7 yuan per 1mol of the product produced according to 86 percent yield.
As an important intermediate for preparing fluorescent dye or medicine, with the increase of the demand of N, N-dialkyl chlorinated fat, how to reduce the production cost is one of the problems which need to be solved at present.
Disclosure of Invention
The invention provides a method for preparing N, N-dialkyl chlorinated aliphatic amine and hydrochloride thereof, which takes cheap substituted diamine as raw material, can prepare N, N-dialkyl chlorinated aliphatic amine in one step in the presence of sodium nitrite and hydrochloric acid, and mixes the N, N-dialkyl chlorinated aliphatic amine with hydrochloric acid solution for further distillation treatment to prepare N, N-dialkyl chlorinated aliphatic amine hydrochloride with more stable physicochemical property.
In order to solve the technical problems, the invention provides the following technical scheme:
the invention provides a preparation method of N, N-dialkyl chlorinated aliphatic amine, which comprises the following steps:
(1) Adding substituted diamine into a precooled hydrochloric acid solution, heating to 5-50 ℃, dropwise adding a sodium nitrite solution, and stirring for reaction after dropwise adding; the substituted diamine is N, N-dimethyl propane diamine or N, N-dimethyl butane diamine;
(2) After the reaction in the step (1) is finished, adjusting the pH value of the reaction solution to 10-14, and standing and separating the solution to obtain the N, N-dialkyl chlorinated aliphatic amine; the N, N-dialkyl chlorinated aliphatic amine is 3-chloro-N, N-dimethyl-1-propylamine or 4-chloro-N, N-dimethyl-1-butylamine.
Further, in the step (1), the concentration of the hydrochloric acid solution is 25% to 31%, and in some embodiments of the present invention, the concentration of the hydrochloric acid solution is 31%.
Further, in the step (1), the temperature of the precooled hydrochloric acid solution is-10-0 ℃, preferably-10-5 ℃.
Further, in the step (1), the concentration of the sodium nitrite solution is 30% to 50%, and in some embodiments of the present invention, the concentration of the sodium nitrite solution is 33%.
Further, in the step (1), the dropping time of the sodium nitrite solution is 1-5 h.
Further, in the step (1), the mass ratio of the substituted diamine to the hydrochloric acid solution to the sodium nitrite solution is 1: 3.5-4.5.
Further, in the step (1), the reaction time of the stirring reaction is 30 min-48 h.
Further, in the step (1), the preferred temperature for the stirring reaction is 30 to 40 ℃.
Further, in the step (2), a sodium hydroxide solution is added to the reaction solution to neutralize the reaction solution to a pH of 10 to 14, preferably 10 to 12.
Further, in the step (2), an aqueous phase and an organic phase are obtained by standing and separating, the aqueous phase is extracted with an organic solvent, and the organic phases are combined. The water phase is extracted for not less than 2 times, so that the product dissolved in the water phase is fully replaced, the yield is improved, and the product in the water phase is prevented from polluting the environment.
Further, the organic solvent is one or more of toluene, benzene and ethyl acetate.
And further, adding a hydrochloric acid solution into a mixed solution obtained by combining the organic phases, and then carrying out distillation treatment to separate out a solid to obtain the hydrochloride of the N, N-dialkyl chlorinated fatty amine.
Further, the concentration of the hydrochloric acid solution is 25% -31%.
Further, the mass ratio of the mixed solution to the hydrochloric acid solution is 1.
Further, the temperature of the distillation treatment is 80-115 ℃.
Further, the mixed solvent obtained by distillation can be recycled after water removal.
Compared with the prior art, the invention has the beneficial effects that:
the invention takes cheap substituted diamine as raw material, can prepare N, N-dialkyl chloro fatty amine in one step in the presence of sodium nitrite and hydrochloric acid, and mix with hydrochloric acid solution and further distill and process and prepare N, N-dialkyl chloro fatty amine hydrochloride with more stable physicochemical property, it is easy to store and transport; compared with the existing preparation method, the method has the advantages that the adopted raw materials are cheap and easy to obtain, the cost of the main raw materials is as low as 28.8 yuan/mol of product, the preparation method is simple to operate, the reaction condition is mild, the yield of the target product is high, and the low-cost and high-yield synthesis method is suitable for large-scale preparation of the N, N-dialkyl chloro aliphatic amine and the hydrochloride thereof.
Detailed Description
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The terminology used in the description of the invention herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed items.
The present invention is further described below in conjunction with specific examples to enable those skilled in the art to better understand the present invention and to practice it, but the examples are not intended to limit the present invention.
Example 1
The embodiment relates to a preparation method of 3-chloro-N, N-dimethyl-1-propylamine and hydrochloride thereof, which comprises the following specific steps:
(1) Preparation of 3-chloro-N, N-dimethyl-1-propylamine
Weighing 500mL of 31% hydrochloric acid solution, cooling to-5 ℃, weighing 102g of N, N-dimethyl propane diamine, dropwise adding the N, N-dimethyl propane diamine into the precooled hydrochloric acid solution, heating the reaction solution to 30 ℃ after dropwise adding, slowly adding 250g of 33% sodium nitrite solution into the reaction solution, and finishing adding for 5 hours. After the dropwise addition, the reaction was stirred for 30min.
After the reaction is finished, adding a sodium hydroxide solution with the concentration of 40% into the reaction liquid to neutralize the reaction liquid until the pH value is 10-12, and standing and separating the reaction liquid to obtain a water phase and an organic phase. Extracting the water phase with xylene for 2 times, mixing the organic phase obtained by extraction with the organic phase obtained by standing and liquid separation to obtain a mixed solution, which is a dispersion liquid of the product. Performing nuclear magnetic characterization on the product, 1 H NMR(DMSO，400MHz):δ3.38(t,2H，J＝7.2Hz),2.36-2.33(m,2H),2.27(s,6H),1.67(t,2H，J＝7.0Hz).
according to nuclear magnetism results, the 3-chloro-N, N-dimethyl-1-propylamine is prepared.
(2) Preparation of 3-chloro-N, N-dimethyl-1-propylamine hydrochloride
To the mixed solution prepared above was added 120g of a hydrochloric acid solution having a concentration of 31%, and the solvent was distilled off under normal pressure to precipitate 137.5g of a solid, which was 87% in yield. Performing nuclear magnetic characterization on the product, 1 H NMR(DMSO，400MHz):δ11.07(br,s,1H),3.8-3.5(m,2H),3.17-3.14(m,2H),2.74(s,6H),2.20-2.18(m,2H).
from the nuclear magnetic results, 3-chloro-N, N-dimethyl-1-propylamine hydrochloride was prepared.
Example 2
This example relates to the preparation of 3-chloro-N, N-dimethyl-1-propylamine and its hydrochloride salt as follows:
(1) Preparation of 4-chloro-N, N-dimethyl-1-butylamine
Measuring 470mL of 31% hydrochloric acid solution, cooling to-5 ℃, weighing 116.2g of N, N-dimethyl propane diamine, dropwise adding into the precooled hydrochloric acid solution, heating the reaction solution to 10 ℃ after dropwise adding, slowly adding 230g of 33% sodium nitrite solution into the reaction solution, and finishing adding for 4.5 hours. After the dropwise addition, the reaction was stirred for 30min.
After the reaction is finished, adding a sodium hydroxide solution with the concentration of 40% into the reaction liquid to neutralize the reaction liquid until the pH value is 10-12, and standing and separating the reaction liquid to obtain a water phase and an organic phase. Extracting the water phase with xylene for 2 times, and mixing the organic phase obtained by extraction with the organic phase obtained by standing and liquid separation to obtain a mixed solution, which is a dispersion of the product. Performing nuclear magnetic characterization on the product, 1 H NMR(DMSO，400MHz):δ3.38(t,2H，J＝7.2Hz),2.36(m，2H)，2.27(s,6H),1.57-1.33(m，4H).
according to the nuclear magnetic results, 4-chloro-N, N-dimethyl-1-butylamine is prepared.
(2) Preparation of 4-chloro-N, N-dimethyl-1-butylamine hydrochloride
To the mixed solution prepared above was added 120g of a hydrochloric acid solution having a concentration of 31%, and the solvent was distilled off under normal pressure to precipitate 145g of a solid in 84% yield. Performing nuclear magnetic characterization on the product, 1 H NMR(DMSO，400MHz):δ11.09(br,s,1H),3.9-3.6(m,2H),3.20-3.12(m,2H),2.75(s,6H),1.90-1.82(m,4H).
from the nuclear magnetic results, 4-chloro-N, N-dimethyl-1-butylamine hydrochloride was prepared.
Example 3
This example relates to the preparation of 3-chloro-N, N-dimethyl-1-propylamine and its hydrochloride salt, which was prepared in the same manner as in example 1 except that the reaction temperature in the step (1) was changed to 50 degrees, as follows
(1) Preparation of 3-chloro-N, N-dimethyl-1-propylamine
Weighing 500mL of 31% hydrochloric acid solution, cooling to-5 ℃, weighing 102g of N, N-dimethyl propane diamine, dropwise adding the N, N-dimethyl propane diamine into the precooled hydrochloric acid solution, heating the reaction solution to 50 ℃ after dropwise adding, slowly adding 250g of 33% sodium nitrite solution into the reaction solution, and finishing adding for 5 hours. After the dropwise addition, the reaction was stirred for 30min.
After the reaction is finished, adding a sodium hydroxide solution with the concentration of 40% into the reaction liquid to neutralize the reaction liquid until the pH value is 10-12, and standing and separating the reaction liquid to obtain a water phase and an organic phase. Extracting the water phase with xylene for 2 times, and mixing the organic phase obtained by extraction with the organic phase obtained by standing and liquid separation to obtain a mixed solution, which is a dispersion of the product.
(2) Preparation of 3-chloro-N, N-dimethyl-1-propylamine hydrochloride
To the mixed solution prepared above was added 120g of a hydrochloric acid solution having a concentration of 31%, and the solvent was distilled off under normal pressure to precipitate 116g of a solid, which was 69.6% in yield. Performing nuclear magnetic characterization on the product to obtain a nuclear magnetic resonance spectrum, 1 H NMR(DMSO，400MHz):δ11.07(br,s,1H),3.8-3.5(m,2H),3.17-3.14(m,2H),2.74(s,6H),2.20-2.18(m,2H).
from the nuclear magnetic results, 3-chloro-N, N-dimethyl-1-propylamine hydrochloride was prepared.
Example 4
This example relates to the preparation of 3-chloro-N, N-dimethyl-1-propylamine and its hydrochloride salt, which was the same as in example 1 except that the dropping time of sodium nitrite in step (1) was changed as follows
(1) Preparation of 3-chloro-N, N-dimethyl-1-propylamine
Weighing 500mL of 31% hydrochloric acid solution, cooling to-5 ℃, weighing 102g of N, N-dimethyl propane diamine, dropwise adding the N, N-dimethyl propane diamine into the precooled hydrochloric acid solution, heating the reaction solution to 20 ℃ after dropwise adding, slowly adding 250g of 33% sodium nitrite solution into the reaction solution, and finishing adding for 1 h. After the dropwise addition, the reaction was stirred for 8 hours.
After the reaction is finished, adding a sodium hydroxide solution with the concentration of 40% into the reaction liquid to neutralize the reaction liquid until the pH value is 10-12, and standing and separating the reaction liquid to obtain a water phase and an organic phase. Extracting the water phase with xylene for 2 times, and mixing the organic phase obtained by extraction with the organic phase obtained by standing and liquid separation to obtain a mixed solution, which is a dispersion of the product.
(2) Preparation of 3-chloro-N, N-dimethyl-1-propylamine hydrochloride
120g of a hydrochloric acid solution having a concentration of 31% was added to the mixed solution prepared above,the solvent was distilled off under normal pressure to precipitate 82.5g of a solid, which was 52.2% in yield. Performing nuclear magnetic characterization on the product, 1 H NMR(DMSO，400MHz):δ11.07(br,s,1H),3.8-3.5(m,2H),3.17-3.14(m,2H),2.74(s,6H),2.20-2.18(m,2H).
from the nuclear magnetic results, 3-chloro-N, N-dimethyl-1-propylamine hydrochloride was prepared.
Comparative example 1
This comparative example relates to the preparation of 3-chloro-N, N-dimethyl-1-propylamine and its hydrochloride salt, which was prepared in the same manner as in example 1 except that the reaction temperature in the step (1) was changed to 0 deg.C, as follows
(1) Preparation of 3-chloro-N, N-dimethyl-1-propylamine
Weighing 500mL of 31% hydrochloric acid solution, cooling to-5 ℃, weighing 102g of N, N-dimethyl propane diamine, dropwise adding the N, N-dimethyl propane diamine into the precooled hydrochloric acid solution, heating the reaction solution to 0 ℃ after dropwise adding, slowly adding 250g of 33% sodium nitrite solution into the reaction solution, and finishing adding for 5 hours. After the dropwise addition, the reaction was stirred for 48 hours.
After the reaction is finished, adding a sodium hydroxide solution with the concentration of 40% into the reaction liquid to neutralize the reaction liquid until the pH value is 10-12, and standing the reaction liquid without layering. The aqueous phase was extracted 2 times with xylene and the gas phase characterization showed no target product.
Comparative example 2
This comparative example relates to the preparation of 3-chloro-N, N-dimethyl-1-propylamine and its hydrochloride salt, which was prepared in the same manner as in example 1 except that the reaction temperature in the step (1) was changed to 60 degrees, as follows
(1) Preparation of 3-chloro-N, N-dimethyl-1-propylamine
Weighing 500mL of 31% hydrochloric acid solution, cooling to-5 ℃, weighing 102g of N, N-dimethyl propane diamine, dropwise adding the N, N-dimethyl propane diamine into the precooled hydrochloric acid solution, heating the reaction solution to 60 ℃ after dropwise adding, slowly adding 250g of 33% sodium nitrite solution into the reaction solution, and finishing adding for 5 hours. After the dropwise addition, the reaction was stirred for 30min.
After the reaction is finished, adding a sodium hydroxide solution with the concentration of 40% into the reaction liquid to neutralize the reaction liquid until the pH value is 10-12, and standing and separating the reaction liquid to obtain a water phase and an organic phase. Extracting the water phase with xylene for 2 times, mixing the organic phase obtained by extraction with the organic phase obtained by standing and liquid separation to obtain a mixed solution, which is a dispersion liquid of the product. The product was gas chromatographed and showed only 13% conversion of the starting material.
Comparative example 3
In the comparative example, 1- (2-aminoethyl) pyrrolidone is used as a reaction raw material, and 1- (2-chloroethyl) pyrrolidone is prepared in one step in the presence of sodium nitrite and hydrochloric acid, wherein the preparation process comprises the following steps:
480mL of 31% hydrochloric acid solution is measured and cooled to-5 ℃, 128.2g of 1- (2-aminoethyl) pyrrolidone is measured and added into the precooled hydrochloric acid solution dropwise, the temperature of the reaction solution is raised to 30 ℃ after the dropwise addition, then 230g of 33% sodium nitrite solution is slowly added into the reaction solution, and the addition is completed within 4.5 h. After the dropwise addition, the reaction was stirred for 30min. LC-MS showed the conversion of the starting material was complete.
After the reaction is finished, adding a sodium hydroxide solution with the concentration of 40% into the reaction liquid to neutralize the reaction liquid until the pH value is 10-12, and standing and separating the reaction liquid to obtain a water phase and an organic phase. Extracting the water phase with xylene for 2 times, and mixing the organic phase obtained by extraction with the organic phase obtained by standing and liquid separation to obtain a mixed solution. LC-MS characterization is carried out on the product, and the result shows that the main product is 1- (2-hydroxyethyl) pyrrolidone, and the target product 1- (2-chloroethyl) pyrrolidone is not prepared.
As can be seen from the above examples and comparative examples, the present application can prepare the corresponding N, N-dialkylchloroaliphatic amines, such as 3-chloro-N, N-dimethyl-1-propylamine or 4-chloro-N, N-dimethyl-1-butylamine, using specific reaction raw materials in the presence of sodium nitrite and hydrochloric acid at a suitable reaction temperature. The preparation method provided by the invention is simple to operate, high in yield and low in raw material cost, for example, N-dimethyl-1, 3-diaminopropane required for preparing 3-chloro-N, N-dimethyl-1-propylamine only needs 25.6 yuan/mol per mol, and the preparation cost of the target product is greatly reduced.
According to the current test results, the preparation method is not suitable for the reaction for preparing the corresponding chlorinated aliphatic amine by using the 1- (2-aminoethyl) pyrrolidone compound as the reaction raw material, and is supposed to be related to the properties of reactants.
The above-mentioned embodiments are merely preferred embodiments for fully illustrating the present invention, and the scope of the present invention is not limited thereto. The equivalent substitution or change made by the technical personnel in the technical field on the basis of the invention is all within the protection scope of the invention. The protection scope of the invention is subject to the claims.
Claims (10)
1. A preparation method of N, N-dialkyl chlorinated aliphatic amine is characterized by comprising the following steps:
(1) Adding substituted diamine into precooled hydrochloric acid solution, heating to 5-50 ℃, dropwise adding sodium nitrite solution, and stirring for reaction after dropwise adding; the substituted diamine is N, N-dimethyl propane diamine or N, N-dimethyl butane diamine;
(2) After the reaction in the step (1) is finished, adjusting the pH value of the reaction solution to 10-14, and standing and separating the solution to obtain the N, N-dialkyl chlorinated aliphatic amine; the N, N-dialkyl chlorinated aliphatic amine is 3-chlorine-N, N-dimethyl-1-propylamine or 4-chlorine-N, N-dimethyl-1-butylamine.
2. The preparation method according to claim 1, wherein in the step (1), the concentration of the hydrochloric acid solution is 25-31%; the temperature of the precooled hydrochloric acid solution is-10-0 ℃.
3. The preparation method according to claim 1, wherein in the step (1), the concentration of the sodium nitrite solution is 30-50%; the dropping time of the sodium nitrite solution is 1-5 h.
4. The production method according to claim 1, wherein in the step (1), the mass ratio of the substituted diamine to the hydrochloric acid solution to the sodium nitrite solution is 1: 3.5-4.5.
5. The method according to claim 1, wherein the stirring reaction in step (1) is carried out for a reaction time of 30min to 48 hours.
6. The production method according to claim 1, wherein in the step (2), the aqueous phase and the organic phase are obtained by performing stationary liquid separation, the aqueous phase is extracted with an organic solvent, and the organic phases are combined.
7. The preparation method according to claim 6, wherein the organic solvent is one or more of toluene, benzene and ethyl acetate.
8. The method according to claim 6, wherein the hydrochloride of the N, N-dialkylchloroaliphatic amine is obtained by adding a hydrochloric acid solution to a mixed solution obtained by combining organic phases and then performing distillation treatment to precipitate a solid.
9. The method according to claim 8, wherein the concentration of the hydrochloric acid solution is 25-31%; the mass ratio of the mixed solution to the hydrochloric acid solution is 1.
10. The method according to claim 8, wherein the temperature of the distillation treatment is 80 to 115 ℃.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09202778A (en) * | 1995-11-22 | 1997-08-05 | Kureha Chem Ind Co Ltd | Conversion of amino group of primary amine to chloro group and chemical synthesis utilizing the same |
| JP2001106672A (en) * | 1999-10-05 | 2001-04-17 | Sumikin Chemical Co Ltd | Method for producing 2,5-dichloropyridine |
| CN102775339A (en) * | 2012-08-14 | 2012-11-14 | 江苏恒祥化工有限责任公司 | Preparation method of N-methyl-2-chloroethylpyrrolidine |
| US9199964B1 (en) * | 2014-07-31 | 2015-12-01 | Dow Agrosciences Llc | Process for the preparation of 3-(3-chloro-1H-pyrazol-1-yl)pyridine |
-
2022
- 2022-08-18 CN CN202210994807.6A patent/CN115246775A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09202778A (en) * | 1995-11-22 | 1997-08-05 | Kureha Chem Ind Co Ltd | Conversion of amino group of primary amine to chloro group and chemical synthesis utilizing the same |
| JP2001106672A (en) * | 1999-10-05 | 2001-04-17 | Sumikin Chemical Co Ltd | Method for producing 2,5-dichloropyridine |
| CN102775339A (en) * | 2012-08-14 | 2012-11-14 | 江苏恒祥化工有限责任公司 | Preparation method of N-methyl-2-chloroethylpyrrolidine |
| US9199964B1 (en) * | 2014-07-31 | 2015-12-01 | Dow Agrosciences Llc | Process for the preparation of 3-(3-chloro-1H-pyrazol-1-yl)pyridine |
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