GB923910A - New piperidine derivatives - Google Patents

New piperidine derivatives

Info

Publication number
GB923910A
GB923910A GB4390761A GB4390761A GB923910A GB 923910 A GB923910 A GB 923910A GB 4390761 A GB4390761 A GB 4390761A GB 4390761 A GB4390761 A GB 4390761A GB 923910 A GB923910 A GB 923910A
Authority
GB
United Kingdom
Prior art keywords
piperidone
general formula
ethylene ketal
ethylene
ketal
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
GB4390761A
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 Diagnostics GmbH
CF Boehringer und Soehne GmbH
Original Assignee
Boehringer Mannheim GmbH
CF Boehringer und Soehne GmbH
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 Boehringer Mannheim GmbH, CF Boehringer und Soehne GmbH filed Critical Boehringer Mannheim GmbH
Publication of GB923910A publication Critical patent/GB923910A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • 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)
  • Plural Heterocyclic Compounds (AREA)

Abstract

The invention comprises piperidine derivatives of the general formula <FORM:0923910/IV(a)/1> wherein X is a direct linkage, an oxygen atom or an alkylene radical -(CH2)nwith n = 1 or 2, which may also be unsaturated, A is a C2-C4 straight or branched chained alkylene radical and Y is <FORM:0923910/IV(a)/2> or <FORM:0923910/IV(a)/3> , the two radicals R being C1-C6 alkyl radicals which may also be joined together to form a common alkylene chain; acid addition salts of these compounds; and processes for preparing the compounds in which (1) a reactive ester of the general formula <FORM:0923910/IV(a)/4> wherein Z is an acid radical, is reacted with a piperidine derivative of the general formula <FORM:0923910/IV(a)/5> wherein Y is <FORM:0923910/IV(a)/6> , (2) an amine of the general formula <FORM:0923910/IV(a)/7> is condensed with a reactive ester of the general formula <FORM:0923910/IV(a)/8> wherein Y is <FORM:0923910/IV(a)/9> , (3) the products of (1) or (2) are hydrolysed to give the corresponding piperidones (Y is =O), (4) the products of (3) are reduced to give the piperidinols (Y is <FORM:0923910/IV(a)/100> , and (5) in all cases, if desired, the product is converted into an acid addition salt. Piperidone-(4)-ethylene ketal is prepared from piperidone-(4)-hydrochloride and ethylene glycol. Trimethylene glycol may be used instead of ethylene glycol to give piperidone-(4)-propylene ketal(1,3), and an analogous preparation of 1-(b -carbethoxy-ethyl)-piperidone-(4)-ethylene ketal is described. 1-(g -Chloropropyl)- piperidone-(4)-ethylene ketal hydrochloride is obtained by the reaction of thionyl chloride on 1-(g -hydroxypropyl)-piperidone-(4)-ethylene ketal which itself is prepared (a) by the lithium aluminium hydride reduction of 1-(b -carbethoxy-ethyl)-piperidone-(4)-ethylene ketal, (b) from piperidone-4-ethylene ketal and trimethylene chlorohydrin or (c) as in (b) with 1-bromo-3-chloropropane replacing the trimethylene chlorohydrin. 5-(g -Chloropropyl)-iminodibenzyl is prepared by adding trimethylene chlorohydrin-p-toluene sulphonic acid ester to the reaction mixture of phenyl lithium and iminodibenzyl. A similar preparation of 5-(g -chloropropyl)-iminostilbene is described.
GB4390761A 1960-12-09 1961-12-07 New piperidine derivatives Expired GB923910A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB0060414 1960-12-09

Publications (1)

Publication Number Publication Date
GB923910A true GB923910A (en) 1963-04-18

Family

ID=6972816

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4390761A Expired GB923910A (en) 1960-12-09 1961-12-07 New piperidine derivatives

Country Status (4)

Country Link
BE (1) BE611302A (en)
CH (1) CH393331A (en)
GB (1) GB923910A (en)
LU (1) LU40924A1 (en)

Also Published As

Publication number Publication date
BE611302A (en) 1962-06-08
LU40924A1 (en) 1962-02-07
CH393331A (en) 1965-06-15

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