GB793010A - Substituted piperidine 4-carboxylic esters - Google Patents

Substituted piperidine 4-carboxylic esters

Info

Publication number
GB793010A
GB793010A GB15792/56A GB1579256A GB793010A GB 793010 A GB793010 A GB 793010A GB 15792/56 A GB15792/56 A GB 15792/56A GB 1579256 A GB1579256 A GB 1579256A GB 793010 A GB793010 A GB 793010A
Authority
GB
United Kingdom
Prior art keywords
aminophenyl
ethyl
phenyl
converted
bromide
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
GB15792/56A
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.)
Merck and Co Inc
Original Assignee
Merck and Co Inc
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 Merck and Co Inc filed Critical Merck and Co Inc
Publication of GB793010A publication Critical patent/GB793010A/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
    • C07D211/56—Nitrogen atoms
    • C07D211/58—Nitrogen atoms attached in position 4
    • 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
    • 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
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
    • C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4

Landscapes

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

Abstract

The invention comprises compounds of the formula <FORM:0793010/IV (b)/1> and acid addition salts thereof, wherein R is hydrogen or an acyl radical, and their preparation by reacting a b -(p-aminophenyl)ethyl halide such as b -(p-aminophenyl) ethyl chloride with 4-phenyl-4-carboethoxypiperidine or an acid addition salt, such as the carbonate, thereof to give the N-[b -(p-aminophenyl) ethyl]-4-carboethoxypiperidine and, for the preparation of compounds wherein R is an acyl group, treating this compound with an acylating agent. The reaction between the 4-phenyl-4-carboethoxypiperidine carbonate or other acid salt and the b -(p-aminophenyl) ethyl halide is preferably carried out by heating the reactants together in an inert liquid medium, for example, a lower alkanol such as ethanol, in the presence of an alkali metal bicarbonate. The products may be converted into salts, for example with hydrogen chloride, hydrogen bromide or sulphuric acid. The compounds are used as analgesics. In examples: (1) b -(p-aminophenyl) ethyl chloride hydrochloride is reacted with 4 - phenyl - 4 - carboethoxy - piperidine carbonate and the resulting N-[b -(p-aminophenyl) ethyl] - 4 - phenyl - 4 - carboethoxy piperidine is converted into its dihydrochloride; (2) the free base obtained in (1) is converted into its N-acetyl derivative and the corresponding monohydrochloride and (3) purified N-[b -(p-aminophenyl) ethyl] - 4 - phenyl - 4 - carboethoxy piperidine, obtained from the dihydrochloride of (1) by reprecipitation and distillation, is converted into its monohydrochloride. Starting materials. b - (p - Aminophenyl)-ethyl chloride hydrochloride, containing also some b -(p-aminophenyl) ethyl bromide hydrochloride, is made by nitrating b -phenylethyl bromide and reducing the resulting b -(p-nitrophenyl) ethyl bromide with stannous chloride.
GB15792/56A 1955-05-26 1956-05-22 Substituted piperidine 4-carboxylic esters Expired GB793010A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US793010XA 1955-05-26 1955-05-26

Publications (1)

Publication Number Publication Date
GB793010A true GB793010A (en) 1958-04-09

Family

ID=22149651

Family Applications (1)

Application Number Title Priority Date Filing Date
GB15792/56A Expired GB793010A (en) 1955-05-26 1956-05-22 Substituted piperidine 4-carboxylic esters

Country Status (1)

Country Link
GB (1) GB793010A (en)

Similar Documents

Publication Publication Date Title
GB1377225A (en) Acylanilino compounds and herbicidal compositions containing them
GB1138405A (en) Morpholine derivatives
GB642412A (en) Process of purifying aromatic 1-hydroxy-2-acid amides by conversion into aromatic oxazine diones and reconversion of the said diones to purified amides
GB1077076A (en) Novel imidazole derivatives and a process for the manufacture thereof
GB793010A (en) Substituted piperidine 4-carboxylic esters
GB774858A (en) Tropane and -Î-tropane derivatives and process for preparation thereof
GB843752A (en) Novel morphinane derivatives and a process for the manufacture thereof
GB853295A (en) Benzoic acid amides and a process for their manufacture
ES384946A1 (en) Novel adamantylurea derivatives and a process for the preparation thereof
GB1109308A (en) Heterocyclic alkanoic acid amides
GB729967A (en) Isonicotinic acid derivatives and process for the manufacture thereof
GB1254928A (en) beta-ALKOXYACRYLIC ACID AMIDES
GB813218A (en) Nor-tropines and nor-pseudo-tropines and process for their production
JPS5522699A (en) Novel 3-amino-1-benzylpyrrolidine derivative
GB771151A (en) Method for the preparation of aminoacyl-anilides
GB846377A (en) 2-substituted-2-propargyl propanediol dicarbamates
GB847779A (en) 2-(4-biphenylyl)-í¸-hexenoic acid esters thereof
GB750194A (en) Isonicotinamides
GB843908A (en) Novel morphinan derivatives and the manufacture thereof
GB1019777A (en) Substituted benzamides
GB726286A (en) Process for the production of 1-p-nitrophenyl-2-dichloroacet-amidopropane-1, 3-diols
GB969790A (en) New aminoalkyl aryloxyalkanoic esters of use as local anaesthetics and a process for their preparation
ES243711A1 (en) A procedure for preparing new therapeutic compounds in the form of free base or acidal salts of non-toxic addiction (Machine-translation by Google Translate, not legally binding)
ES414449A1 (en) Procedure for the obtaining of (1- (m-trifluorometilfenil) -indazol-3-il) -a-alkyloxyacetamides and their adición salts. (Machine-translation by Google Translate, not legally binding)
GB786384A (en) Basic alkoxyalkyl esters of phenothiazine-10-carboxylic acid and process for preparing same