CN110294721A - The synthesis technology of 1- acetyl group -4- [3- (methyl oxygroup) -4- nitrobenzophenone] piperazine - Google Patents
The synthesis technology of 1- acetyl group -4- [3- (methyl oxygroup) -4- nitrobenzophenone] piperazine Download PDFInfo
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- CN110294721A CN110294721A CN201910660041.6A CN201910660041A CN110294721A CN 110294721 A CN110294721 A CN 110294721A CN 201910660041 A CN201910660041 A CN 201910660041A CN 110294721 A CN110294721 A CN 110294721A
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- piperazine
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- nitrobenzophenone
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- acetyl group
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
Abstract
The invention discloses the synthesis technologies of 1- acetyl group -4- [3- (methyl oxygroup) -4- nitrobenzophenone] piperazine; it is related to medication chemistry related fields; by optimizing reaction process; by two-step reaction single stepping; it is cheap to reach reaction raw materials; operation is simple, high income, post-processes simple feature.Heating reaction 12 hours after the DMF solution of the piperazine of the fluoro- 2- Nitroanisole of the 5- of 200 grams of 1eq and 302 grams of 3eq stirs 30 minutes, the acetic anhydride of 358 grams of 3eq is slowly added into reaction solution, reaction solution is stirred at room temperature 12 hours, water dilution is added into reaction solution, it is washed twice after solid filtering, product is obtained after 50 degree of dryings, the filtrate of filtering can be used to recycle 1- acetylpiperazine.
Description
Technical field
The present invention relates to medication chemistry related fields, specially 1- acetyl group -4- [3- (methyl oxygroup) -4- nitrobenzophenone]
The synthesis technology of piperazine.
Background technique
1- acetyl group -4- [3- (methyl oxygroup) -4- nitrobenzophenone] piperazine English name is 1- (4- (3-methoxy-4-
Nitrophenyl) piperazin-1-yl) ethanone, No. CAS is 1116229-11-8, molecular formula C13H17N3O4, molecule
Amount is 279.29178.
1- acetyl group -4- [3- (methyl oxygroup) -4- nitrobenzophenone] piperazine is there are three types of synthetic method in document at present, and every kind
The shortcomings that synthetic method, is as follows:
Method 1:
Disadvantage: multistep reaction operation, reaction yield is low, and purification process is complicated；
Method 2:
Disadvantage: reaction route is long, and operation is complicated, needs to be filtered for multiple times and dry, reaction yield is low, and purification process is multiple
It is miscellaneous；
Method 3:
Disadvantage: initial reaction raw material (1- acetylpiperazine) is expensive.
Summary of the invention
The purpose of the present invention is to provide the synthesis works of 1- acetyl group -4- [3- (methyl oxygroup) -4- nitrobenzophenone] piperazine
Skill, by two-step reaction single stepping, reaches that reaction raw materials are cheap, and operation is simple by optimizing reaction process, high income,
Post-process simple feature.
To achieve the above object, the invention provides the following technical scheme: 1- acetyl group -4- [3- (methyl oxygroup) -4- nitro
Phenyl] piperazine synthesis technology, reaction product I
It is by the fluoro- 2- Nitroanisole II of 5-
With piperazine III
It is reacted with acetic anhydride IV
Ac2O。
Preferably, including following preparation step:
Heating reaction 12 hours after the DMF solution of the fluoro- 2- Nitroanisole of step 1:5- and piperazine stirs 30 minutes；
Step 2: acetic anhydride is slowly added in reaction solution, reaction solution is stirred at room temperature 12 hours；
Step 3: water dilution is added to reaction solution, is filtered；
Step 4: solid washing twice, obtains yellow solid after dry after filtering.
Preferably, the fluoro- 2- Nitroanisole quality of the 5- is 200 grams, equivalent 1；
The piperazine quality is 302 grams, equivalent 3；
The acetic anhydride quality is 358 grams, equivalent 3.
Preferably, in the step 4, drying temperature is 50 DEG C.
Preferably, in the step 4, yellow solid is reaction product I, and the quality of yellow solid is 284 grams, and reaction produces
The yield of object I is 87%.
Preferably, in the step 3, filtered filtrate can be used to recycle 1- acetylpiperazine, and the 1- acetyl piperazine recycled
Piperazine quality is 270 grams, the rate of recovery 90%.
Compared with prior art, the beneficial effects of the present invention are:
The present invention is by optimization reaction process, by two-step reaction single stepping, and the reaction raw materials price that the present invention uses
Cheaply, have filter operation in reaction process, by filtrate recycling can obtain by-product 1- acetylpiperazine, allow byproduct of reaction by
It recycles, entire operation is simple, and reaction yield is high, can reach 85% or more, and reaction controllability is good, post-reaction treatment letter
It is single, stable product quality, to reach the new process of product mass production.
Specific embodiment
The following is a clear and complete description of the technical scheme in the embodiments of the invention, it is clear that described embodiment
Only a part of the embodiment of the present invention, instead of all the embodiments.
A kind of embodiment provided by the invention: the synthesis of 1- acetyl group -4- [3- (methyl oxygroup) -4- nitrobenzophenone] piperazine
Technique is as follows:
Compared to
With
The preparation method in two kinds of paths, two-step reaction single stepping of the present invention, operation is simple, and purification process is simple,
And 87% reaction yield, reaction yield is high.
Compared toPreparation method,
The present invention uses the fluoro- 2- Nitroanisole of 5- and piperazine as initial reaction product, compared to the 1- acetylpiperazine prices of raw materials
It is cheaper, high financial profit, and 1- acetylpiperazine can also be recycled in filtrate of the invention, 1- acetylpiperazine is the preparation method
One of raw material, and it is expensive, illustrate that the product for preparing of the invention can be two kinds of value products, good economy performance.
It is of the invention that specific preparation process is as follows: the fluoro- 2- Nitroanisole of 5- (200 grams, 1eq) and piperazine (302 grams,
After DMF solution 3eq) stirs 30 minutes after heating reaction 12 hours, be slowly added into reaction solution acetic anhydride (358 grams,
3eq), reaction solution is stirred at room temperature 12 hours.
Water dilution is added into reaction solution, is washed twice after solid filtering, it is yellow solid that product is obtained after 50 degree of dryings
(284 grams, 87%).Filtrate can be used to recycle 1- acetylpiperazine (270 grams, 90%).MS(ES+):280.1[M+1]+.1HNMR
Spectrum:(400MHz,DMSO-d6)δ2.06(s,3H),3.35-3.59(m,8H),3.92(s,3H),6.52-6.53(d,
2H),7.90-7.92(d,1H)。
It is obvious to a person skilled in the art that invention is not limited to the details of the above exemplary embodiments, Er Qie
In the case where without departing substantially from spirit or essential attributes of the invention, the present invention can be realized in other specific forms.Therefore, no matter
From the point of view of which point, the present embodiments are to be considered as illustrative and not restrictive, and the scope of the present invention is by appended power
Benefit requires rather than above description limits, it is intended that all by what is fallen within the meaning and scope of the equivalent elements of the claims
Variation is included within the present invention.
Claims (6)
- The synthesis technology of 1.1- acetyl group -4- [3- (methyl oxygroup) -4- nitrobenzophenone] piperazine, it is characterised in that reaction product IIt is by the fluoro- 2- Nitroanisole II of 5-With piperazine IIIIt is reacted with acetic anhydride IVAc2O。
- 2. the synthesis technology of 1- acetyl group -4- [3- (methyl oxygroup) -4- nitrobenzophenone] piperazine according to claim 1, It is characterised in that it includes following preparation step:Heating reaction 12 hours after the DMF solution of the fluoro- 2- Nitroanisole of step 1:5- and piperazine stirs 30 minutes；Step 2: acetic anhydride is slowly added in reaction solution, reaction solution is stirred at room temperature 12 hours；Step 3: water dilution is added to reaction solution, is filtered；Step 4: solid washing twice, obtains yellow solid after dry after filtering.
- 3. the synthesis technology of 1- acetyl group -4- [3- (methyl oxygroup) -4- nitrobenzophenone] piperazine according to claim 2, It is characterized by:The fluoro- 2- Nitroanisole quality of the 5- is 200 grams, equivalent 1；The piperazine quality is 302 grams, equivalent 3；The acetic anhydride quality is 358 grams, equivalent 3.
- 4. the synthesis technology of 1- acetyl group -4- [3- (methyl oxygroup) -4- nitrobenzophenone] piperazine according to claim 2, It is characterized by: drying temperature is 50 DEG C in the step 4.
- 5. the synthesis technology of 1- acetyl group -4- [3- (methyl oxygroup) -4- nitrobenzophenone] piperazine according to claim 2, It is characterized by: yellow solid is reaction product I, and the quality of yellow solid is 284 grams, reaction product I in the step 4 Yield be 87%.
- 6. the synthesis technology of 1- acetyl group -4- [3- (methyl oxygroup) -4- nitrobenzophenone] piperazine according to claim 2, It is characterized by: filtered filtrate can be used to recycle 1- acetylpiperazine, and the 1- acetylpiperazine matter recycled in the step 3 Amount is 270 grams, the rate of recovery 90%.
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| CN201910660041.6A CN110294721A (en) | 2019-07-22 | 2019-07-22 | The synthesis technology of 1- acetyl group -4- [3- (methyl oxygroup) -4- nitrobenzophenone] piperazine |
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| CN101827848A (en) * | 2007-08-08 | 2010-09-08 | 葛兰素史密丝克莱恩有限责任公司 | 2- [ (2-{phenylamino}-1H-pyrrolo [2, 3-d] pyrimidin-4-yl) amino] benzamide derivatives as iIGF-1R inhibitors for the treatment of cancer |
| CN104703983A (en) * | 2012-08-10 | 2015-06-10 | 韩国化学研究院 | N2,N4-bis(4-(piperazine-1-yl)phenyl)pirimidine-2,4-diamine derivative or pharmaceutically acceptable salt thereof, and composition containing same as active ingredient for preventing or treating cancer |
| CN105218561A (en) * | 2014-06-25 | 2016-01-06 | 上海艾力斯医药科技有限公司 | Annelated pyrimidines ring derivatives, its preparation method and application |
| CN105384694A (en) * | 2014-08-22 | 2016-03-09 | 四川海思科制药有限公司 | Substituted aminopyrimidine derivative, preparation method therefor and pharmaceutical application thereof |
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2019
- 2019-07-22 CN CN201910660041.6A patent/CN110294721A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101827848A (en) * | 2007-08-08 | 2010-09-08 | 葛兰素史密丝克莱恩有限责任公司 | 2- [ (2-{phenylamino}-1H-pyrrolo [2, 3-d] pyrimidin-4-yl) amino] benzamide derivatives as iIGF-1R inhibitors for the treatment of cancer |
| CN104703983A (en) * | 2012-08-10 | 2015-06-10 | 韩国化学研究院 | N2,N4-bis(4-(piperazine-1-yl)phenyl)pirimidine-2,4-diamine derivative or pharmaceutically acceptable salt thereof, and composition containing same as active ingredient for preventing or treating cancer |
| CN105218561A (en) * | 2014-06-25 | 2016-01-06 | 上海艾力斯医药科技有限公司 | Annelated pyrimidines ring derivatives, its preparation method and application |
| CN105384694A (en) * | 2014-08-22 | 2016-03-09 | 四川海思科制药有限公司 | Substituted aminopyrimidine derivative, preparation method therefor and pharmaceutical application thereof |
Non-Patent Citations (1)
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