GB881893A - Arylpiperidine derivatives - Google Patents

Arylpiperidine derivatives

Info

Publication number
GB881893A
GB881893A GB1277958A GB1277958A GB881893A GB 881893 A GB881893 A GB 881893A GB 1277958 A GB1277958 A GB 1277958A GB 1277958 A GB1277958 A GB 1277958A GB 881893 A GB881893 A GB 881893A
Authority
GB
United Kingdom
Prior art keywords
aryl
radical
phenyl
formula
alk
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
GB1277958A
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.)
Individual
Original Assignee
Individual
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 NL110185D priority Critical patent/NL110185C/xx
Application filed by Individual filed Critical Individual
Priority to GB1277958A priority patent/GB881893A/en
Priority to FR792189A priority patent/FR1458901A/en
Priority to DE1959J0016315 priority patent/DE1289845B/en
Priority to CH7224759A priority patent/CH397677A/en
Priority to BE577977A priority patent/BE577977A/en
Publication of GB881893A publication Critical patent/GB881893A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/32—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen
    • C07C1/325—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a metal atom
    • C07C1/326—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a metal atom the hetero-atom being a magnesium atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
    • C07C17/2632—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions involving an organo-magnesium compound, e.g. Grignard synthesis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/46—Friedel-Crafts reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
    • 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
    • C07D211/38—Halogen atoms or nitro radicals
    • 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
    • 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
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom

Landscapes

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

Abstract

The invention comprises aroylalkyl piperidinols of the formula <FORM:0881893/IV (b)/1> and acid addition salts and non-toxic quaternary salts thereof wherein Ar is a halophenyl (e.g. fluoro-, chloro-, bromo-oriodo-phenyl), methoxy-, ethoxy- or dimethoxy-phenyl or thienyl radical or a monocyclic aromatic hydrocarbon radical of less than 9 carbon atoms, Ar1 is a halophenyl radical or a monocyclic aromatic hydrocarbon radical of less than 9 carbon atoms (e.g. phenyl, tolyl or xylyl), and Alk is a lower alkylene radical of 3-6 carbon atoms, e.g. propyl, and their preparation by reacting a compound of the formula Ar-CO-Alk-Halogen with a 4-Ar1-piperidin-4-ol. The compounds are used pharmaceutically, suitably in the form of salts such as the hydrohalides, sulphates, phosphates, sulphamates, citrates, lactates, maleates, malates, succinates, tartrates, cinnamates, acetates, benzoates, gluconates and ascorbates. They also form quaternary salts with quaternating agents such as alkyl, aralkyl, alkenyl and hydroxyalkyl halides, sulphates and aryl-sulphonates. Aryl haloalkyl ketones of the formula Ar CO.Alk.Halogen used as starting materials are made either by treating benzene or a substituted benzene, with a haloalkanoyl halide, by the Friedel-Crafts reaction, using aluminium chloride or a milder catalyst, such as stannic chloride, or by reacting an aryl magnesium bromide Grignard reagent with a haloalkanonitrile, followed by acid hydrolysis of the adduct. 4-Aryl piperidin-4-ols, in which the aryl group may be substituted according to the definition of the group Ar1 above, are made by treating a 4-aryl-1:2:3:6-tetrahydropyridine, obtainable by condensing an a -methylstyrene with ammonium chloride and formaldehyde, with hydrogen bromide to give a 4-bromo-4-aryl-piperidine which is hydrolysed with aqueous sodium hydroxide. a -Methylstyrenes of the formula Ar1C(CH3) : CH2, such as p-fluoro-a -methylstyrene, are made by treating the corresponding acetophenone with methyl magnesium bromide and dehydrating the product or by treating the Grignard reagent derived from an aryl halide; e.g. p-chlorophenyl magnesium bromide with acetone and dehydrating the resulting carbinol. The Provinional Specification relates to compounds of the above general formula wherein Ar is a phenyl, alkylphenyl, halophenyl, alkoxyphenol or thienyl radical, Alk is a 1:3 propylene radical and Ar1 is a phenyl, halophenyl or alkyphenyl radical. Specification 881,894 is referred to.
GB1277958A 1958-04-22 1958-04-22 Arylpiperidine derivatives Expired GB881893A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
NL110185D NL110185C (en) 1958-04-22
GB1277958A GB881893A (en) 1958-04-22 1958-04-22 Arylpiperidine derivatives
FR792189A FR1458901A (en) 1958-04-22 1959-04-15 Process for the manufacture of aroylpiperidin derivatives and in particular of 1-aroyl alkyl-4-aryl-4-piperidinols
DE1959J0016315 DE1289845B (en) 1958-04-22 1959-04-18 4- (4'-Hydroxy-4'-phenylpiperidino) -butyrophenones, their acid addition salts and processes for their preparation
CH7224759A CH397677A (en) 1958-04-22 1959-04-20 Process for the preparation of aroylalkylpiperidines
BE577977A BE577977A (en) 1958-04-22 1959-04-21 Novel aroylpiperidine derivatives and process for their preparation.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1277958A GB881893A (en) 1958-04-22 1958-04-22 Arylpiperidine derivatives

Publications (1)

Publication Number Publication Date
GB881893A true GB881893A (en) 1961-11-08

Family

ID=10010962

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1277958A Expired GB881893A (en) 1958-04-22 1958-04-22 Arylpiperidine derivatives

Country Status (5)

Country Link
BE (1) BE577977A (en)
CH (1) CH397677A (en)
DE (1) DE1289845B (en)
GB (1) GB881893A (en)
NL (1) NL110185C (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3484446A (en) * 1967-01-16 1969-12-16 Aldrich Chem Co Inc 1-(3-(4-fluorobenzoyl)propyl) - and 1 - (1,1-ethylenedioxy - 1 - (4 - fluorophenyl)-4-butyl)-4-piperidyl carbamates
USH1209H (en) 1985-10-04 1993-07-06 The United States Of America As Represented By The United States Department Of Energy No-carrier-added (18F)-N-methylspiroperidol
US5521209A (en) * 1992-06-19 1996-05-28 Basf Aktiengesellschaft N-substituted azabicyclo[3.2.0]heptane derivatives as neuroleptics, the preparation and use thereof
US20100004289A1 (en) * 2005-04-29 2010-01-07 Clera Inc. Substituted butyrophenone derivatives

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3408356A (en) * 1965-08-31 1968-10-29 Squibb & Sons Inc Long chain esters of 4'-fluoro-4-[4-hydroxy-4-(alpha, alpha, alpha-trifluorotolyl)piperi-dino]butyrophenone and the like
DE4341403A1 (en) * 1993-12-04 1995-06-08 Basf Ag N-substituted 3-azabicycloalkane derivatives, their preparation and use
EP2767275A1 (en) 2013-02-13 2014-08-20 Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. Nortriptyline, haloperidol or prochlorperazine edisylate for use in the treatment of tuberculosis as well as two screening methods

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3484446A (en) * 1967-01-16 1969-12-16 Aldrich Chem Co Inc 1-(3-(4-fluorobenzoyl)propyl) - and 1 - (1,1-ethylenedioxy - 1 - (4 - fluorophenyl)-4-butyl)-4-piperidyl carbamates
USH1209H (en) 1985-10-04 1993-07-06 The United States Of America As Represented By The United States Department Of Energy No-carrier-added (18F)-N-methylspiroperidol
US5521209A (en) * 1992-06-19 1996-05-28 Basf Aktiengesellschaft N-substituted azabicyclo[3.2.0]heptane derivatives as neuroleptics, the preparation and use thereof
SG82540A1 (en) * 1992-06-19 2001-08-21 Basf Ag N-substituted azabicyclo [3.2.0] heptane derivatives as neuroleptics, the preparation and use thereof
US20100004289A1 (en) * 2005-04-29 2010-01-07 Clera Inc. Substituted butyrophenone derivatives

Also Published As

Publication number Publication date
DE1289845B (en) 1969-02-27
CH397677A (en) 1965-08-31
NL110185C (en)
BE577977A (en) 1959-08-17

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