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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 amides

Info

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
Application number
GB434/57A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Saab Bofors AB
Original Assignee
Bofors AB
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Bofors AB filed Critical Bofors AB
Publication of GB800565A publication Critical patent/GB800565A/en
Expired legal-status Critical Current

Links

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.
GB434/57A 1956-01-23 1957-01-04 Method of producing n-alkyl-piperidine-ª‡-monocarboxylic acid amides and n-alkyl-pyrrolidine-ª‡-monocarboxylic acid amides Expired GB800565A (en)

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)

* Cited by examiner, † Cited by third party
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

Cited By (4)

* Cited by examiner, † Cited by third party
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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