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GB826803A - Improvements in or relating to new 4-carbalkoxy-4-phenyl piperidine derivatives and processes for preparing them - Google Patents

Improvements in or relating to new 4-carbalkoxy-4-phenyl piperidine derivatives and processes for preparing them

Info

Publication number
GB826803A
GB826803A GB2850357A GB2850357A GB826803A GB 826803 A GB826803 A GB 826803A GB 2850357 A GB2850357 A GB 2850357A GB 2850357 A GB2850357 A GB 2850357A GB 826803 A GB826803 A GB 826803A
Authority
GB
United Kingdom
Prior art keywords
carbethoxy
phenyl
ketone
phenylpiperidyl
propiophenone
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
GB2850357A
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.)
Janssen Pharmaceutica NV
Nederlandsche Combinatie voor Chemische Industrie NV
Original Assignee
Janssen Pharmaceutica NV
Nederlandsche Combinatie voor Chemische Industrie 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 Janssen Pharmaceutica NV, Nederlandsche Combinatie voor Chemische Industrie NV filed Critical Janssen Pharmaceutica NV
Publication of GB826803A publication Critical patent/GB826803A/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
    • C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
    • C07D211/64—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4 having an aryl radical as the second substituent in position 4

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises compounds of the general formula <FORM:0826803/IV (b)/1> wherein A represents an alkylene group containing from 2 to 4 carbon atoms, B is an alkyl or alkenyl group of not more than 5 carbon atoms, n is zero or one, and R is an unsaturated cycloparaffin radical, or an unsubstituted or substituted phenyl, thienyl, furyl or pyridyl radical, and their preparation (a) by reacting an o -haloalkyl or o -tosyloxy ketone of general formula R(CH : CH)nCO.A.X, where X is halogen or tosyloxy, with a 4-carbalkoxy-4-phenyl pipidine; (b) by reacting formaldehyde, or a compound which yields it during the reaction, a 4carbalkoxy-4-phenylpiperidine or a salt thereof, and a ketone RCOCH3 under conditions of the Mannich reaction; or (c) by reacting a 4-carbalkoxy-4-phenylpiperidine or a salt thereof, with an a : b -unsaturated ketone R.CO.CH= CH2. In examples: (1) 4-carbethoxy-4-phenyl piperidine hydrochloride, paraformaldehyde, acetophenone, concentrated HCl and isopropanol are refluxed giving o -(4-carbethoxy4 - phenyl - piperidyl - 1) propiophenone hydrochloride; (2) as in (1) using propiophenone or 2-propionyl thiophene to give a -methylb - (4 - carbethoxy - 4 - phenylpiperidyl - 1) propiophenone or 2 - [a - methyl - b - (4 - carbethoxy - 4 - phenylpiperidyl - 1) - propionyl] thiophene respectively; (3) and (4), as in (1) are prepared 3-hydroxy-, 4-hydroxy-, 3-dimethylamino- and 4-dimethylamino-o -(4-carbethoxy - 4 - phenylpiperidyl - 1) propiophenone hydrochlorides; (5) 4 - carbethoxy - 4 - phenylpiperidine in toluene is treated dropwise with phenyl propenyl ketone or propenyl thienyl ketone yielding b -(4-carbethoxy-4-phenyl-piperidyl-1) butyrophenone (as its HCl salt) or 2-[b (4 - carbethoxy - 4 - phenylpiperidyl - 1) butyryl] thiophene respectively; (6) as in (5) phenyl vinyl ketone gives o -(4-carbethoxy-4phenyl - piperidyl - 1) propiophenone hydrochloride; (7) 4-carbo-n-propoxy-4-phenyl-piperidine, o -chlorobutyrophenone and KI are heated in xylene giving g -(4-carbo-n-propoxy-4-phenylpiperidyl - 1) butyrophenone hydrochloride. Many other products are listed.
GB2850357A 1956-10-04 1957-09-10 Improvements in or relating to new 4-carbalkoxy-4-phenyl piperidine derivatives and processes for preparing them Expired GB826803A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
NL211144 1956-10-04

Publications (1)

Publication Number Publication Date
GB826803A true GB826803A (en) 1960-01-20

Family

ID=29268053

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2850357A Expired GB826803A (en) 1956-10-04 1957-09-10 Improvements in or relating to new 4-carbalkoxy-4-phenyl piperidine derivatives and processes for preparing them

Country Status (2)

Country Link
GB (1) GB826803A (en)
NL (1) NL90758C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3462427A (en) * 1965-06-16 1969-08-19 Boehringer Sohn Ingelheim Novel 1-(cycloalkylidene-ethyl-4-phenyl-piperidines

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3462427A (en) * 1965-06-16 1969-08-19 Boehringer Sohn Ingelheim Novel 1-(cycloalkylidene-ethyl-4-phenyl-piperidines

Also Published As

Publication number Publication date
NL90758C (en)

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