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GB584877A - A process for the manufacture of heterocyclic bases - Google Patents

A process for the manufacture of heterocyclic bases

Info

Publication number
GB584877A
GB584877A GB243745A GB243745A GB584877A GB 584877 A GB584877 A GB 584877A GB 243745 A GB243745 A GB 243745A GB 243745 A GB243745 A GB 243745A GB 584877 A GB584877 A GB 584877A
Authority
GB
United Kingdom
Prior art keywords
phenyl
methyl
benzyl
pyrrolidine
cyano
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
GB243745A
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.)
ALBERT RONALD MOSS
Roche Products Ltd
Original Assignee
ALBERT RONALD MOSS
Roche Products Ltd
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 ALBERT RONALD MOSS, Roche Products Ltd filed Critical ALBERT RONALD MOSS
Priority to GB243745A priority Critical patent/GB584877A/en
Publication of GB584877A publication Critical patent/GB584877A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07D207/08—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 hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
    • 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
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

Heterocyclic bases of the general formula <FORM:0584877/IV/1> in which R is an aryl group, R1 an alkyl or substituted alkyl group, R2 an alkyl group and n is 2 or 3, are obtained by hydrogenating catalytically an acetonitrile of the general formula <FORM:0584877/IV/2> The nitriles I may be converted to the corresponding ketone by treatment with a Grignard reagent. In examples: (1) 1-methyl-1-benzyl-1 - (g - phenyl - g - acetyl - g - cyano - propyl) amine prepared by condensing acetyl benzyl cyanide with methyl-chloroethyl-benzylamine in the presence of sodamide, is hydrogenated in the presence of palladised charcoal to 1 : 2-dimethyl-3-cyano-3-phenyl-pyrrolidine. After hydrolysis and esterification n-propyl 1 : 2-dimethyl - 3 - phenyl - pyrrolidine - 3 - carboxylate is obtained; (2) 1-methyl-1-benzyl-1-(g -phenyl-g - propionyl - g - cyano - propyl) amine prepared by condensing propionyl benzyl cyanide with methyl-chloroethyl-benzyl-amine in the presence of sodamide, is hydrogenated with palladised charcoal when 1-methyl-2-ethyl-3-phenyl-3-cyano-pyrrolidine is obtained. This is hydrolysed and esterified to n-amyl 1-methyl-2-ethyl-3-phenyl-pyrrolidine-3-carboxylate; (3) 1 : 2-dimethyl-3-phenyl-3-cyanopyrrolidine is reacted with phenyl magnesium bromide to obtain 1 : 2 - dimethyl - 3 - phenyl - 3 - benzoyl - pyrrolidine; (4) 1 : 2-dimethyl-3-phenyl-cyanopyrrolidine is reacted with cyclohexyl magnesium bromide to obtain 1 : 2-dimethyl-3-phenyl-3-hexahydro-benzoyl-pyrrolidine; (5) 1-methyl-1-benzyl-1-(g -propionyl-g -phenyl-g -cyano) butylamine prepared by condensing propionyl benzyl cyanide with methyl-g -chloropropyl-benzyl-amine, in the presence of sodamide, is hydrogenated with palladised charcoal when 1 - methyl - 2 - ethyl - 3 - phenyl - 3 - cyano - piperidine is obtained.
GB243745A 1945-01-31 1945-01-31 A process for the manufacture of heterocyclic bases Expired GB584877A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB243745A GB584877A (en) 1945-01-31 1945-01-31 A process for the manufacture of heterocyclic bases

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB243745A GB584877A (en) 1945-01-31 1945-01-31 A process for the manufacture of heterocyclic bases

Publications (1)

Publication Number Publication Date
GB584877A true GB584877A (en) 1947-01-24

Family

ID=9739555

Family Applications (1)

Application Number Title Priority Date Filing Date
GB243745A Expired GB584877A (en) 1945-01-31 1945-01-31 A process for the manufacture of heterocyclic bases

Country Status (1)

Country Link
GB (1) GB584877A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2585210A (en) * 1949-02-26 1952-02-12 Sterling Drug Inc Piperidine carboxylic acid esters

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2585210A (en) * 1949-02-26 1952-02-12 Sterling Drug Inc Piperidine carboxylic acid esters

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