GB895049A - N-substituted-4-aryl-4-acyloxy piperidines - Google Patents

N-substituted-4-aryl-4-acyloxy piperidines

Info

Publication number
GB895049A
GB895049A GB39030/60A GB3903060A GB895049A GB 895049 A GB895049 A GB 895049A GB 39030/60 A GB39030/60 A GB 39030/60A GB 3903060 A GB3903060 A GB 3903060A GB 895049 A GB895049 A GB 895049A
Authority
GB
United Kingdom
Prior art keywords
aryl
cyanide
piperidinol
reacting
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
GB39030/60A
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.)
ILSE LIEBRECHT
JULIUS LIEBRECHT
WALTER MAYER LIST
WALTER MAYER-LIST
Original Assignee
ILSE LIEBRECHT
JULIUS LIEBRECHT
WALTER MAYER LIST
WALTER MAYER-LIST
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 ILSE LIEBRECHT, JULIUS LIEBRECHT, WALTER MAYER LIST, WALTER MAYER-LIST filed Critical ILSE LIEBRECHT
Publication of GB895049A publication Critical patent/GB895049A/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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

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

Abstract

The invention comprises compounds of the general formula <FORM:0895049/IV (b)/1> and their addition salts with inorganic and organic acids, wherein R represents an alkyl group, R1 and R2 which may be the same or different represent hydrogen atoms or alkyl groups, R3 represents an aryl group and R4 represents C4-10 branched or unbranched saturated or unsaturated aliphatic hydrocarbon residue, if desired, interrupted by an oxygen or sulphur atom or an imino or N-alkylimino group, and the preparation thereof by (a) condensing a 4-aryl-4-piperidinol with a haloalkylcyanide and esterifying the resulting N-cyanoalkyl-4-aryl-4-piperidinol; (b) condensing a 4-aliphatic acyloxy-4-aryl-piperidine with a haloalkyl cyanide; (c) reacting an N-cyanoalkyl-piperidine-(4) with a Grignard reagent R3MgX (where X is a chlorine bromine or iodine atom) or with R3Li and esterifying the resulting piperidinol; and (d) reacting a 4-aryl 4-piperidinol with a dihalogeno compound X-R4-X and reacting the 4-haloalkyl-4-aryl-4-piperidinol with a metal cyanide and esterifying the free -OH group. The process under (c) may be combined with one wherein the piperidone is prepared by reacting a substituted or unsubstituted N-cyanoalkyliminodipropionic acid dialkyl ester with a strong base and with a further process wherein the above ester is prepared by reacting an amine NCR4NH2 with an acrylic acid alkyl ester CH2=CR1-COOR5 (where R5 is an alkyl group). o -Chlorohexyl cyanide, o -bromopentyl cyanide and o -bromodecyl cyanide are prepared from the dihaloalkane and potassium cyanide. The compounds of the invention may be contained in analgesic compositions in a form suitable for oral, parenteral or rectal administration (e.g. tablets, capsules, dragees, linctuses, syrups, injection solutions or suppositories).
GB39030/60A 1959-11-13 1960-11-14 N-substituted-4-aryl-4-acyloxy piperidines Expired GB895049A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE895049X 1959-11-13

Publications (1)

Publication Number Publication Date
GB895049A true GB895049A (en) 1962-04-26

Family

ID=6847511

Family Applications (1)

Application Number Title Priority Date Filing Date
GB39030/60A Expired GB895049A (en) 1959-11-13 1960-11-14 N-substituted-4-aryl-4-acyloxy piperidines

Country Status (1)

Country Link
GB (1) GB895049A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2158108A1 (en) * 1971-11-03 1973-06-15 Synthelabo 1-(3-cyano-3,3-diphenylpropyl)-4-phenyl-4-piperidinols - with analgesic antitussive and spasmolytic activity

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2158108A1 (en) * 1971-11-03 1973-06-15 Synthelabo 1-(3-cyano-3,3-diphenylpropyl)-4-phenyl-4-piperidinols - with analgesic antitussive and spasmolytic activity

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