GB940534A - Process for the preparation of new piperidine derivatives - Google Patents

Process for the preparation of new piperidine derivatives

Info

Publication number
GB940534A
GB940534A GB10480/62A GB1048062A GB940534A GB 940534 A GB940534 A GB 940534A GB 10480/62 A GB10480/62 A GB 10480/62A GB 1048062 A GB1048062 A GB 1048062A GB 940534 A GB940534 A GB 940534A
Authority
GB
United Kingdom
Prior art keywords
aryl
formula
group
compound
reacting
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
GB10480/62A
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.)
Boehringer Ingelheim Pharma GmbH and Co KG
Original Assignee
Dr Karl Thomae 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 Dr Karl Thomae GmbH filed Critical Dr Karl Thomae GmbH
Publication of GB940534A publication Critical patent/GB940534A/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
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen 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
    • C07D211/36—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
    • C07D211/52—Oxygen atoms attached in position 4 having an aryl radical as the second substituent in position 4

Landscapes

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

Abstract

The invention comprises compounds of the general formula <FORM:0940534/C2/1> and their non-toxic acid addition salts, in which R1 represents methyl or ethyl, R2 and R3, which may be the same or different, represent hydrogen atoms, methyl or ethyl groups R4 represents a methyl, ethyl-, methoxy- or ethoxy-substituted aryl or unsubstituted aryl group, A represents a saturated or unsaturated, straight or branched-chain alkylene group containing 5-8 carbon atoms which may be interrupted by one or more oxygen, and/or sulphur atoms and X represents a halogen atom or a thiocyanate or a nitro group, and the preparation thereof by (a) (wherein X represents a halogen atom or a nitro group) by reacting a 4-aryl-4-hydroxy piperidine of the formula <FORM:0940534/C2/2> with a compound Hal-A-X and esterifying the resulting compound, or (b) (wherein A is an unsaturated alkylene group) by reacting an appropriate 4-aryl-4-acyloxypiperidine (preferably in the form of a salt with a weak acid) with Hal-A-X, or (c) reacting a piperidone-(4) of the formula <FORM:0940534/C2/3> with an aryl- or methyl-, ethyl-, methoxy-, or ethoxy-aryl-Grignard or aryl lithium compound to give the corresponding 4-hydroxy piperidine and esterifying the hydroxy group, or (d) quaternising an N-allyl-piperidine of the formula <FORM:0940534/C2/4> <FORM:0940534/C2/5> with a compound Hal-A-X, removing the N-allyl group and, if necessary, esterifying the free hydroxy group, or (e) (wherein X is an iodine atom, a thio cyanate or a nitro group) by reacting a compound of the formula I (wherein X is bromine) with an alkali metal iodide, thiocyanate or nitrite. Compounds of formula VI are prepared by (a) reaction of an alkyl acrylate with a haloalkylamine, subsequent internal ester condensation, saponification and decarboxylation, (b) reaction of a di-(b -alkoxycarbonylethyl)-amine with dihaloalkyl compounds followed by internal condensation saponification and decarboxylation or (c) Mannich reaction starting from a nitro-or haloalkylamine, formaldehyde and diethylketone or a -alkyl or a ,a -dialkylacetone-dicarboxylic acid-alkyl esters and subsequent saponification and decarboxylation. N-allyl-4-aryl-4-acyloxy-piperidines are prepared by N-allylation and O-esterification of a 4-aryl-4-hydroxy piperidine. Pharmaceutical compositions comprise the compounds I or their acid addition salts in association with a pharmaceutical carrier and may be presented as tablets, ampoules or suppositories. The compound I show analgesic and antitussive properties.
GB10480/62A 1961-03-18 1962-03-19 Process for the preparation of new piperidine derivatives Expired GB940534A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB0061756 1961-03-18

Publications (1)

Publication Number Publication Date
GB940534A true GB940534A (en) 1963-10-30

Family

ID=6973319

Family Applications (1)

Application Number Title Priority Date Filing Date
GB10480/62A Expired GB940534A (en) 1961-03-18 1962-03-19 Process for the preparation of new piperidine derivatives

Country Status (2)

Country Link
FR (1) FR1914M (en)
GB (1) GB940534A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2234241A (en) * 1989-07-19 1991-01-30 Inst Khim Nauk Akademii Nauk K 1-(2-Ethoxyethyl)-4-phenyl-4-propionyloxypiperidine and salts thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2234241A (en) * 1989-07-19 1991-01-30 Inst Khim Nauk Akademii Nauk K 1-(2-Ethoxyethyl)-4-phenyl-4-propionyloxypiperidine and salts thereof
GB2234241B (en) * 1989-07-19 1992-07-22 Inst Khim Nauk Akademii Nauk K 1-(2-ethoxyethyl)-4-phenyl-4-propionyloxypiperidine and salts thereof

Also Published As

Publication number Publication date
FR1914M (en) 1963-07-15

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