GB965848A - 1-(3,3-diphenyl-3-alkanoyl)propylspiro-1,4-piperidines - Google Patents

1-(3,3-diphenyl-3-alkanoyl)propylspiro-1,4-piperidines

Info

Publication number
GB965848A
GB965848A GB38266/62A GB3826662A GB965848A GB 965848 A GB965848 A GB 965848A GB 38266/62 A GB38266/62 A GB 38266/62A GB 3826662 A GB3826662 A GB 3826662A GB 965848 A GB965848 A GB 965848A
Authority
GB
United Kingdom
Prior art keywords
reacting
halide
compound
cyano
give
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
GB38266/62A
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.)
Research Laboratorium C Janssen NV
Original Assignee
Research Laboratorium C Janssen NV
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 Research Laboratorium C Janssen NV filed Critical Research Laboratorium C Janssen NV
Publication of GB965848A publication Critical patent/GB965848A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/20—Spiro-condensed ring systems
    • 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
    • C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • 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
    • C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/20—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C07D211/22—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/10—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

The invention comprises compounds of the general formula: <FORM:0965848/C1/1> and their non-toxic acid addition (including ascorbic acid) and quaternary ammonium salts wherein X represents a cyano or a CO(C1-7 alkyl) group, n is 1 or 2 and R is a hydrogen atom or a methyl group. The compounds are prepared by reacting an amine of the formula: <FORM:0965848/C1/2> with a diphenyl-cyano propyl halide of the formula: <FORM:0965848/C1/3> and optionally reacting the cyano compound with a C1-7 alkyl-magnesium halide. The piperidines used as starting materials are prepared by reacting a hydroaryl ketone with ethyl a -cyano acetate to give a compound: <FORM:0965848/C1/4> reacting this with sodium ethoxide and a -cyanoacetamide to produce a compound: <FORM:0965848/C1/5> hydrolysing this to form the diacid: <FORM:0965848/C1/6> reducing the acid to give the di-alcohol, treating the alcohol with hydrogen halide to form the di-halide, reacting the di-halide with benzylamine to give a compound: <FORM:0965848/C1/7> and debenzylating this either by hydrogenolysis or with cyanogen bromide followed by hydrolysis of the N-cyanoamide.
GB38266/62A 1961-10-10 1962-10-09 1-(3,3-diphenyl-3-alkanoyl)propylspiro-1,4-piperidines Expired GB965848A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US14401861A 1961-10-10 1961-10-10

Publications (1)

Publication Number Publication Date
GB965848A true GB965848A (en) 1964-08-06

Family

ID=22506705

Family Applications (1)

Application Number Title Priority Date Filing Date
GB38266/62A Expired GB965848A (en) 1961-10-10 1962-10-09 1-(3,3-diphenyl-3-alkanoyl)propylspiro-1,4-piperidines

Country Status (3)

Country Link
DK (1) DK103235C (en)
FR (1) FR2358M (en)
GB (1) GB965848A (en)

Also Published As

Publication number Publication date
DK103235C (en) 1965-12-06
FR2358M (en) 1964-02-24

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