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GB576962A - New piperidine derivatives - Google Patents

New piperidine derivatives

Info

Publication number
GB576962A
GB576962A GB851144A GB851144A GB576962A GB 576962 A GB576962 A GB 576962A GB 851144 A GB851144 A GB 851144A GB 851144 A GB851144 A GB 851144A GB 576962 A GB576962 A GB 576962A
Authority
GB
United Kingdom
Prior art keywords
piperidone
methyl
tetramethyl
hydroxy
aryl
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
GB851144A
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.)
GEOFFREY MALCOLM BADGER
JAMES LLAN HENDRY
Imperial Chemical Industries Ltd
Original Assignee
GEOFFREY MALCOLM BADGER
JAMES LLAN HENDRY
Imperial Chemical Industries Ltd
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 GEOFFREY MALCOLM BADGER, JAMES LLAN HENDRY, Imperial Chemical Industries Ltd filed Critical GEOFFREY MALCOLM BADGER
Priority to GB851144A priority Critical patent/GB576962A/en
Publication of GB576962A publication Critical patent/GB576962A/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
    • 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

N-Substituted 4-aryl-4-hydroxy-piperidines of the formula <FORM:0576962/IV/1> wherein Ar represents an aryl group optionally substituted, for example by alkyl groups, Alk represents an alkyl radical and R1, R2, R3 and R4 may each represent hydrogen or an alkyl group, are obtained by a Grignard reaction between the correspondingly substituted 4-piperidone and an appropriate aryl magnesium halide and subsequently hydrolysing the organomagnesium compound so produced. The products may readily be converted into their hydrochlorides, picrates or esters. Specified starting-materials are: N-methyl-2 : 2 : 6-trimethyl - 4 - piperidone, N - methyl - 2 : 2 : 6 : 6-tetramethyl-4-piperidone, N-ethyl-2 : 2 : 6 : 6-tetramethyl-4-piperidone, N-methyl-4-piperidone and N - allyl - 2 : 2 : 6 : 6 - tetramethyl-4-piperidone. In examples: (1) an ether solution of the Grignard reagent made from bromobenzene and magnesium is added to an ether solution of N-methyl-2 : 2 : 6 : 6-tetramethyl-4-piperidone, the product is treated with concentrated hydrochloric acid and the reaction mixture is worked up to obtain 4-hydroxy-4-phenyl - N - methyl - 2 : 2 : 6 : 6 - tetramethyl - piperidone, readily convertible into the 4-acetoxy derivative; (2) 4-hydroxy-4-phenyl-N-methyl-piperidine is obtained from N-methyl-4-piperidone by the method of (1). N-Methyl-4-piperidone is obtained by the hydrolysis and decarboxylation of 3-carbomethoxy-N-methylpiperidone.
GB851144A 1944-05-05 1944-05-05 New piperidine derivatives Expired GB576962A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB851144A GB576962A (en) 1944-05-05 1944-05-05 New piperidine derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB851144A GB576962A (en) 1944-05-05 1944-05-05 New piperidine derivatives

Publications (1)

Publication Number Publication Date
GB576962A true GB576962A (en) 1946-04-29

Family

ID=9853854

Family Applications (1)

Application Number Title Priority Date Filing Date
GB851144A Expired GB576962A (en) 1944-05-05 1944-05-05 New piperidine derivatives

Country Status (1)

Country Link
GB (1) GB576962A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4680302A (en) * 1985-02-01 1987-07-14 Laboratoire L. Lafon 1-alkyl-3-hydroxy-3-phenylpiperidines

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4680302A (en) * 1985-02-01 1987-07-14 Laboratoire L. Lafon 1-alkyl-3-hydroxy-3-phenylpiperidines

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