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GB834290A - Substituted piperidines - Google Patents

Substituted piperidines

Info

Publication number
GB834290A
GB834290A GB4905/57A GB490557A GB834290A GB 834290 A GB834290 A GB 834290A GB 4905/57 A GB4905/57 A GB 4905/57A GB 490557 A GB490557 A GB 490557A GB 834290 A GB834290 A GB 834290A
Authority
GB
United Kingdom
Prior art keywords
radical
hydroxy
stands
alkyl
methyl
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
GB4905/57A
Inventor
Edwin Harry Paterson Young
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.)
Imperial Chemical Industries Ltd
Original Assignee
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
Priority to NL98891D priority Critical patent/NL98891C/xx
Priority to NL101733D priority patent/NL101733C/xx
Priority to US3126393D priority patent/US3126393A/en
Priority to BE564780D priority patent/BE564780A/xx
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB4905/57A priority patent/GB834290A/en
Priority to FR758214A priority patent/FR1282517A/en
Publication of GB834290A publication Critical patent/GB834290A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
    • C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
    • 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
    • C07D211/10—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 radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
    • C07D211/12—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 radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with only hydrogen atoms attached to the ring nitrogen atom
    • 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
    • C07D211/48—Oxygen atoms attached in position 4 having an acyclic carbon atom 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
    • C07D211/56—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
    • C07D211/68—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 one double bond between ring members or between a ring member and a non-ring member
    • C07D211/70—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 one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
    • C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
    • C07D295/03—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/06—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals
    • C07D295/067—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain

Landscapes

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

Abstract

The invention comprises compounds of the general formula <FORM:0834290/IV (b)/1> wherein R stands for hydrogen or for an alkyl radical or for an alkenyl radical of not more than 6 carbon atoms, the alkyl radical being optionally substituted by halogen atoms, free hydroxy etherified or esterified hydroxy groups, R1, R2, R3 and R4, which may be the same o different, stand for methyl or ethyl radicals, and the piperidine ring (A) may optionally be further substituted by a lower alkyl radical (C1-6), a phenyl radical, or a dialkylaminoalkylamino radical, provided that when the ring A contains no further substituents in positions 3, 4 or 5, then R, R1, R2, R3, R4 together contain more than 4 carbon atoms; non-toxic pharmaceutically-acceptable acid addition salts and quaternary salts wherein the ring nitrogen atom is linked to two methyl radicals, i.e. where R stands for methyl and the nitrogen atom is further methylated; and the preparation thereof: (1) by reducing compounds of the general formula <FORM:0834290/IV (b)/2> preferably by the Clemmensen or Wolf-Kishner methods; (2) by reducing the corresponding tetrahydropyridine compounds of the formula <FORM:0834290/IV (b)/3> where the ring (B) may optionally be further substituted by a lower alkyl or a phenyl radical, the reduction being carried out preferably by using hydrogen and a hydrogenation catalyst or by using sodium ethanol; (3) by alkylation of a compound of the formula <FORM:0834290/IV (b)/4> preferably by the use of an alkyl or alkenyl halide or sulphate or an alkyl sulphonate and in the presence of an acid-binding agent, or when R is a methyl or b -hydroxethyl radical by a formaldehyde/formic acid mixture or ethylene chlorohydrin respectively; (4) (wherein R stands for an alkyl radical containing a terminal acyloxy radical) by acylating the corresponding compounds wherein R stands for an alkyl radical containing a terminal hydroxy group, preferably by use of an acid anhydride or acid chloride in the presence of an inert solvent; (5) (wherein R stands for an alkyl radical containing a terminal alkoxy group), by reacting the corresponding compound wherein R is an alkyl radical containing a terminal halogen atom and an alkali metal alkoxide, preferably in the presence of the alcohol from which the alkoxide is derived; (6) (for the quaternary ammonium compounds) by methylating the corresponding tertiary bases wherein R stands for a methyl radical, preferably by an alkyl halide in the presence of an inert solvent; and (7) (wherein the piperidine ring (A) is substituted in the 4-position by a dialkylaminoalkylamino radical) by reductive alkylation of the corresponding 4-piperidone with a dialkylaminoalkylamine in the presence of hydrogen, and a platinum hydrogenation catalyst. The invention also comprises the preparation of 1 - b - chloroethyl - 2:2:6:6 - tetramethylpiperidine by reacting the corresponding hydroxy ethyl compound with thionyl chloride. The Provisional Specification further discloses that R1, R2, R3 and R4 may be hydro carbon radicals which may be substituted, for example, by a hydroxy group, the ring (A) may be further substituted by a halogen atom, amino, acylamino, alkoxy or hydrocarbon radicals, the last named of which may be optionally substituted by hydroxy or alkoxy radicals or halogen atoms. 1:2:2:6:6 - Pentamethyl - D 3,4 - tetrahydropyridine hydrochloride is prepared from thionyl chloride and 4 - hydroxy - 1:2:2:6:6 - pentamethylpiperidine; and 4-ethyl-4-hydroxy-2:2:6:6-tetramethylpiperidine and its hydriodide are prepared by reducing 4-ethynyl-4-hydroxy2:2:6:6-tetramethylpiperidine.
GB4905/57A 1957-02-13 1957-02-13 Substituted piperidines Expired GB834290A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
NL98891D NL98891C (en) 1957-02-13
NL101733D NL101733C (en) 1957-02-13
US3126393D US3126393A (en) 1957-02-13 X-gamma-dffithylaminopropylamino
BE564780D BE564780A (en) 1957-02-13
GB4905/57A GB834290A (en) 1957-02-13 1957-02-13 Substituted piperidines
FR758214A FR1282517A (en) 1957-02-13 1958-02-13 Manufacturing process for new piperidine derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB4905/57A GB834290A (en) 1957-02-13 1957-02-13 Substituted piperidines

Publications (1)

Publication Number Publication Date
GB834290A true GB834290A (en) 1960-05-04

Family

ID=9786082

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4905/57A Expired GB834290A (en) 1957-02-13 1957-02-13 Substituted piperidines

Country Status (4)

Country Link
US (1) US3126393A (en)
BE (1) BE564780A (en)
GB (1) GB834290A (en)
NL (2) NL101733C (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
USB559701I5 (en) * 1973-09-17 1976-03-23
US4131599A (en) 1975-05-28 1978-12-26 Sankyo Company, Limited Stabilization of poly(mono-olefins)
EP0128285A1 (en) * 1983-06-13 1984-12-19 Hüls Aktiengesellschaft Process for the preparation of polyalkylpiperidyl amines

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3072668A (en) * 1961-09-25 1963-01-08 Warner Lambert Pharmaceutical 1, 4-bis(tetramethyl-4-hydroxy-4-piperidyl) butadiyne
US3513170A (en) * 1966-07-23 1970-05-19 Sankyo Co Preparation of 2,2,6,6-tetramethyl-4-oxopiperidine
US3941744A (en) * 1971-06-05 1976-03-02 Sankyo Company Limited Piperidine derivatives and their use as stabilizers
US3898303A (en) * 1972-05-31 1975-08-05 Sankyo Co Piperidine-spiro-hydantoin derivatives and their use as stabilizers
US3975357A (en) * 1973-04-19 1976-08-17 Sankyo Company Limited Stabilized synthetic polymer compositions
JPS58168634A (en) * 1982-03-31 1983-10-05 Adeka Argus Chem Co Ltd Stabilized synthetic resin composition

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB103541A (en) * 1916-02-05 1917-02-01 Hilda Mary Judd Improvement in the Manufacture of alpha alpha Dimethyl-gamma-hydroxy-piperidines substituted in the alpha1 position, including their N-methyl Derivatives.
US2596450A (en) * 1946-10-28 1952-05-13 Shell Dev Corrosion-inhibiting coating composition containing organic amine nitrites
NL88063C (en) * 1950-12-05
US2636881A (en) * 1951-01-06 1953-04-28 Sharp & Dohme Inc 3-substituted, 3-aryl, 2-pipecolines and salts thereof
US2773870A (en) * 1953-06-04 1956-12-11 Sterling Drag Inc 1-(lower alkyl)-4-phenyl-4-(tertiaryaminoalkoxymethyl- and tertiary-aminoalkoxy) piperidines and their preparation
US2907764A (en) * 1956-07-30 1959-10-06 Searle & Co Heterocyclic esters of 3, 4, 5-trimethoxybenzoic acid

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
USB559701I5 (en) * 1973-09-17 1976-03-23
US4131599A (en) 1975-05-28 1978-12-26 Sankyo Company, Limited Stabilization of poly(mono-olefins)
EP0128285A1 (en) * 1983-06-13 1984-12-19 Hüls Aktiengesellschaft Process for the preparation of polyalkylpiperidyl amines

Also Published As

Publication number Publication date
BE564780A (en)
NL98891C (en)
NL101733C (en)
US3126393A (en) 1964-03-24

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