GB800565A - Method of producing n-alkyl-piperidine-ª‡-monocarboxylic acid amides and n-alkyl-pyrrolidine-ª‡-monocarboxylic acid amides - Google Patents
Method of producing n-alkyl-piperidine-ª‡-monocarboxylic acid amides and n-alkyl-pyrrolidine-ª‡-monocarboxylic acid amidesInfo
- Publication number
- GB800565A GB800565A GB434/57A GB43457A GB800565A GB 800565 A GB800565 A GB 800565A GB 434/57 A GB434/57 A GB 434/57A GB 43457 A GB43457 A GB 43457A GB 800565 A GB800565 A GB 800565A
- Authority
- GB
- United Kingdom
- Prior art keywords
- xylidide
- ester
- give
- acid
- pyrrolidine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 abstract 6
- 150000002148 esters Chemical class 0.000 abstract 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 2
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 abstract 1
- AEVKDASMDDANST-UHFFFAOYSA-N 2-amino-3-ethoxy-3-oxopropanoic acid Chemical compound CCOC(=O)C(N)C(O)=O AEVKDASMDDANST-UHFFFAOYSA-N 0.000 abstract 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 1
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000004157 Nitrosyl chloride Substances 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- JINBYESILADKFW-UHFFFAOYSA-N aminomalonic acid Chemical compound OC(=O)C(N)C(O)=O JINBYESILADKFW-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000006114 decarboxylation reaction Methods 0.000 abstract 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 abstract 1
- 235000019392 nitrosyl chloride Nutrition 0.000 abstract 1
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 abstract 1
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
Abstract
N - Alkyl - piperidine or pyrrolidine - a -carboxylic acid amides of the formula: <FORM:0800565/IV (b)/1> in which R is an alkyl group and Ar a 2-alkylphenyl or 2 : 6-dialkylphenyl radical are made by nitrosating a malonic acid arylamide ester of the general formula: <FORM:0800565/IV (b)/2> in which R1 is an alkyl group, reducing the product to give an aminomalonic acid arylamide ester, reacting with a 1 : 3-trimethylene or 1 : 4-tetramethylene dihalide to give a compound of the general formula: <FORM:0800565/IV (b)/3> in which n is 3 or 4, treating with mineral acid to effect ring closure and decarboxylation to form the piperidine or pyrrolidine carboxylic acid arylamide, the nuclear nitrogen atom of which is then alkylated. In examples: (1) 2 : 6-xylidine is heated with diethylmalonate to give malonic acid dixylidide and malonic ester monoxylidide, the latter is nitrosated with nitrosyl chloride in chloroform to give isonitrosomalonic ester xylidide which is reduced with zinc and formic acid to aminomalonic ester xylidide, treated with 1 : 4-tetramethylene dibromide to give bromobutylaminomalonic ester xylidide, boiled with concentrated hydrochloric acid to give pipecolyl xylidide and alkylated with diethyl sulphate to the desired N-ethylpipecolyl-2 : 6-xylidide, and (2) aminomalonic ethyl ester 2 : 6-xylidide is treated with 1 : 3-trimethylenedibromide and the resulting bromopropylaminomalonic ester xylidide is treated as in (1) to give pyrrolidine a -carboxylic acid xylidide and its N-methyl derivative.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE800565X | 1956-01-23 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB800565A true GB800565A (en) | 1958-08-27 |
Family
ID=20341535
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB434/57A Expired GB800565A (en) | 1956-01-23 | 1957-01-04 | Method of producing n-alkyl-piperidine-ª‡-monocarboxylic acid amides and n-alkyl-pyrrolidine-ª‡-monocarboxylic acid amides |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB800565A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4695576A (en) * | 1984-07-09 | 1987-09-22 | Astra Lake Medel Aktiebolag | L-N-n-propylpipecolic acid-2,6-xylidide |
US4870086A (en) * | 1986-01-03 | 1989-09-26 | Astra Lakemedel Aktiebolag | Optically pure compound and a process for its preparation |
CN103073484A (en) * | 2013-01-28 | 2013-05-01 | 山东诚创医药技术开发有限公司 | Preparation method of mepivacaine and optical enantiomer of mepivacaine |
-
1957
- 1957-01-04 GB GB434/57A patent/GB800565A/en not_active Expired
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4695576A (en) * | 1984-07-09 | 1987-09-22 | Astra Lake Medel Aktiebolag | L-N-n-propylpipecolic acid-2,6-xylidide |
US4870086A (en) * | 1986-01-03 | 1989-09-26 | Astra Lakemedel Aktiebolag | Optically pure compound and a process for its preparation |
CN103073484A (en) * | 2013-01-28 | 2013-05-01 | 山东诚创医药技术开发有限公司 | Preparation method of mepivacaine and optical enantiomer of mepivacaine |
CN103073484B (en) * | 2013-01-28 | 2014-10-22 | 山东诚创医药技术开发有限公司 | Preparation method of mepivacaine and optical enantiomer of mepivacaine |
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