GB563665A - Manufacture of heterocyclic bases - Google Patents

Manufacture of heterocyclic bases

Info

Publication number
GB563665A
GB563665A GB382743A GB382743A GB563665A GB 563665 A GB563665 A GB 563665A GB 382743 A GB382743 A GB 382743A GB 382743 A GB382743 A GB 382743A GB 563665 A GB563665 A GB 563665A
Authority
GB
United Kingdom
Prior art keywords
phenyl
methyl
cyano
ethyl
bases
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
GB382743A
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.)
Roche Products Ltd
Original Assignee
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 Roche Products Ltd filed Critical Roche Products Ltd
Priority to GB382743A priority Critical patent/GB563665A/en
Publication of GB563665A publication Critical patent/GB563665A/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
    • C07D211/02—Preparation by ring-closure or hydrogenation
    • 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)
  • Hydrogenated Pyridines (AREA)

Abstract

Secondary and tertiary heterocyclic bases of the formula <FORM:0563665/IV/1> where n is 1 or 2, R1 is aryl which may contain substituents not interfering with the reaction, R2 is alkyl, aryl or esterified carboxylic group, R3, R4 and R6 are H or alkyl groups, are prepared by condensing the alkali metal (sodium) salts of arylacetonitriles, R1(R2)CHCN with 1,2-or 1,3-dihaloparaffins in alcoholic solution to form halo compounds, R1(R2).(CN).C.(CHR3)n -CH(R4)X, X being halogen, reacting the halo compounds with alkylbenzyl- or dibenzylamines to produce tertiary bases R1(R2(CN).C. (CHR3)n-CH(R4).N(R5).CH2Ph, where R5\h is a benzyl or alkyl radical, and subjecting the tertiary bases to catalytic hydrogenation during which ring formation with elimination of ammonia and toluene takes place. Thus ethyl phenyl-cyanoacetate is condensed in an alcoholic solution of sodium ethylate with 1,3-chlorobromo-propane to form a -phenyl-a -cyano-d -chlorovaleric acid which is heated in a closed vessel with dibenzylamine to form the hydrochloride of a -phenyl-a -cyano-d -dibenzylaminovaleric acid ethyl ester. By hydrogenation with palladium charcoal catalyst 3-phenyl-3-carbethoxypiperidine is formed. In the same way ethylphenyl-cyanoacetate and ethylene dibromide are condensed and the product treated with methyl-benzylamine to form ethyl a - phenyl - a - cyano - d - methyl - benzylaminobutyrate which by reduction gives N-methyl-3-phenyl - 3 - carbethoxy - pyrrolidine. Ethyl a -phenyl - a - cyano - d - methyl - benzyl - amino - valerate, prepared from ethyl a -phenyl-a -cyano-d -chlorovalerate and methyl-benzylamine is hydrogenated to give N-methyl-3-phenyl-3-carbethoxy-piperidine.
GB382743A 1943-03-09 1943-03-09 Manufacture of heterocyclic bases Expired GB563665A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB382743A GB563665A (en) 1943-03-09 1943-03-09 Manufacture of heterocyclic bases

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB382743A GB563665A (en) 1943-03-09 1943-03-09 Manufacture of heterocyclic bases

Publications (1)

Publication Number Publication Date
GB563665A true GB563665A (en) 1944-08-24

Family

ID=9765680

Family Applications (1)

Application Number Title Priority Date Filing Date
GB382743A Expired GB563665A (en) 1943-03-09 1943-03-09 Manufacture of heterocyclic bases

Country Status (1)

Country Link
GB (1) GB563665A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2446804A (en) * 1943-03-09 1948-08-10 Hoffmann La Roche 3-aryl-3-carbalkoxy piperidines and pyrrolidines and synthesis thereof
US2671798A (en) * 1949-04-09 1954-03-09 Merck & Co Inc 2, 2-diphenyl-3-methyl-4-chlorobutyronitrile and processes for preparing the same

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2446804A (en) * 1943-03-09 1948-08-10 Hoffmann La Roche 3-aryl-3-carbalkoxy piperidines and pyrrolidines and synthesis thereof
US2671798A (en) * 1949-04-09 1954-03-09 Merck & Co Inc 2, 2-diphenyl-3-methyl-4-chlorobutyronitrile and processes for preparing the same

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