GB1032646A - Cyclopentyl acetic acid ester derivatives - Google Patents

Cyclopentyl acetic acid ester derivatives

Info

Publication number
GB1032646A
GB1032646A GB4465263A GB4465263A GB1032646A GB 1032646 A GB1032646 A GB 1032646A GB 4465263 A GB4465263 A GB 4465263A GB 4465263 A GB4465263 A GB 4465263A GB 1032646 A GB1032646 A GB 1032646A
Authority
GB
United Kingdom
Prior art keywords
cyclopentyl
prepared
carbon atoms
methyl
group
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
GB4465263A
Inventor
Bent Preben Arnkjaer
Steen Hove Antonsen
Hans Otto Andersen
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.)
Alfred Benzon AS
Original Assignee
Alfred Benzon AS
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 Alfred Benzon AS filed Critical Alfred Benzon AS
Priority to DK555364A priority Critical patent/DK108917C/en
Publication of GB1032646A publication Critical patent/GB1032646A/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
    • C07D211/08—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)

Abstract

The invention comprises quaternary ammonium salts of the general formula: <FORM:1032646/C2/1> where R represents an alkyl group of 4 to 6 carbon atoms, a cycloalkyl group of 5 to 6 carbon atoms, an aralkyl group where the alkyl parts has 1 to 3 carbon atoms, a phenyl group or a phenyl group substituted by a halogen or alkyl group of 1 to 3 carbon atoms; R1 and R2 are the same or different and represent alkyl groups of 1 to 4 carbon atoms; X is an acid residue preferably a halogen or a p-toluene sulphonate group and Y is a direct link or an alkylene group of 1 to 4 carbon atoms. Quaternary ammonium salts are prepared by quaternizing the corresponding bases with substances such as alkyl halides, dialkyl sulphides and alkyl esters of p-toluene sulphonic acid. The bases are prepared by treating a -R-substituted cyclopentyl acetic acid chlorides, where R is the same as before, which are prepared by treating the free acid with thionyl chloride, with 1-methyl-4-hydroxypiperidine. g - (1 - methyl - 4 - piperidyl)propyl a -cyclopentyl phenyl acetate is prepared by reacting g - (1 - methyl - 4 - piperidyl)propanol with a -cyclopentyl-phenyl acetyl chloride. g - (1 - methyl - 4 - piperidyl)propanol is prepared by hydrogenating g -(4-pyridyl)propanol and treating the resulting g -(4-piperidyl)propanol with methyl iodide. Diethyl cyclopentyl cyclohexenyl malonate is prepared by reacting diethyl cyclopentyl malonate with 1,2-dibromocyclohexane. a -Cyclopentyl cyclohexyl acetic acid is prepared by treating diethyl cyclopentyl cyclohexenyl malonate with alcoholic potassium hydroxide followed by hydrochloric acid, ether extraction and heat treatment to give a -cyclopentyl cyclohexenyl acetic acid which is hydrogenated to give the desired product. a -Cyclopentyl-n-hexyl acetic acid is similarly prepared (omitting the hydrogenation) from diethyl cyclopentyl n-hexyl malonate which is prepared from diethyl cyclopentyl malonate and 1-bromohexane. a -Cyclopentyl-p-methyl phenyl acetonitrile and a -cyclopentyl-p-chlorophenyl acetonitrile are prepared by reacting the corresponding p-substituted phenyl acetonitrile with bromocyclopentane. The corresponding substituted acetic acids are prepared by hydrolysis of the nitriles. 1-ethyl-4-hydroxy piperidine is prepared by reacting 4 - hydroxypiperidine with ethyl bromide.
GB4465263A 1963-11-12 1963-11-12 Cyclopentyl acetic acid ester derivatives Expired GB1032646A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DK555364A DK108917C (en) 1963-11-12 1964-11-11 Process for the preparation of quaternary ammonium salts of cyclopentylacetic acid esters.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB4465363 1963-11-12

Publications (1)

Publication Number Publication Date
GB1032646A true GB1032646A (en) 1966-06-15

Family

ID=10434219

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4465263A Expired GB1032646A (en) 1963-11-12 1963-11-12 Cyclopentyl acetic acid ester derivatives

Country Status (2)

Country Link
DK (1) DK107936C (en)
GB (1) GB1032646A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4022787A (en) 1975-07-18 1977-05-10 Carter-Wallace, Inc. Anticholinergic ester and salts thereof
FR2467846A1 (en) * 1979-10-22 1981-04-30 Dufour J C Cyclo:alkyl piperidyl beta hydroxy ester(s) - having anticholinergic and spasmolytic activity for stomach ulcers gastritis etc.
US5294719A (en) * 1991-12-26 1994-03-15 Mitsubishi Petrochemical Company Limited Cyclohexylamine compounds useful as a stabilizer for organic materials
WO2007141289A1 (en) * 2006-06-09 2007-12-13 Beiersdorf Ag Piperidinium compounds and cosmetic compositions containing them

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4022787A (en) 1975-07-18 1977-05-10 Carter-Wallace, Inc. Anticholinergic ester and salts thereof
FR2467846A1 (en) * 1979-10-22 1981-04-30 Dufour J C Cyclo:alkyl piperidyl beta hydroxy ester(s) - having anticholinergic and spasmolytic activity for stomach ulcers gastritis etc.
US5294719A (en) * 1991-12-26 1994-03-15 Mitsubishi Petrochemical Company Limited Cyclohexylamine compounds useful as a stabilizer for organic materials
WO2007141289A1 (en) * 2006-06-09 2007-12-13 Beiersdorf Ag Piperidinium compounds and cosmetic compositions containing them
US7851633B2 (en) 2006-06-09 2010-12-14 Beiersdorf Ag Piperidinium compounds and cosmetic compositions containing them
US8633225B2 (en) 2006-06-09 2014-01-21 Beiersdorf Ag Piperidinium compounds and cosmetic compositions containing them

Also Published As

Publication number Publication date
DK107936C (en) 1967-07-24

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