GB781193A - Improvements in or relating to the production of -ß-substituted carboxylic acid anilides and their derivatives - Google Patents

Improvements in or relating to the production of -ß-substituted carboxylic acid anilides and their derivatives

Info

Publication number
GB781193A
GB781193A GB3153354A GB3153354A GB781193A GB 781193 A GB781193 A GB 781193A GB 3153354 A GB3153354 A GB 3153354A GB 3153354 A GB3153354 A GB 3153354A GB 781193 A GB781193 A GB 781193A
Authority
GB
United Kingdom
Prior art keywords
carboxylic acid
acid anilide
piperidino
monoalkylamino
anilides
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
GB3153354A
Inventor
Emil Hofstetter
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.)
Ed Geistlich Soehne AG fuer Chemische Industrie
Original Assignee
Ed Geistlich Soehne AG fuer Chemische Industrie
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 Ed Geistlich Soehne AG fuer Chemische Industrie filed Critical Ed Geistlich Soehne AG fuer Chemische Industrie
Priority to GB3153354A priority Critical patent/GB781193A/en
Publication of GB781193A publication Critical patent/GB781193A/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
    • C07D295/04—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
    • C07D295/14—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/145—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/15—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero 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

Carboxylic acid anilides of the general formula <FORM:0781193/IV (a)/1> in which R is an unsubstituted or substituted phenyl group, R1 is a hydrocarbon residue, e.g. an alkyl group, and R2 is a monoalkylamino residue or (except when R is a substituted phenyl group) an N-piperidyl group, are made by reducing the corresponding a :b -unsaturated compound with aluminium amalgam. The reaction is preferably carried out in an organic solvent, suitably in an alcoholic solvent such as methanol, and at room temperature. The b -substituted carboxylic acid anilides may optionally have one or more substituents such as alkyl, alkoxy, nitro, amino or halogen substituents, in the benzene nucleus. The monoalkylamino derivatives obtained by the above process may be alkylated to form the corresponding dialkylamine compounds. In examples: (1) b -ethylamino crotonic acid anilide is reduced with aluminium amalgam to b -monoethylaminobutyric acid anilide which is treated with ethyl bromide to give the corresponding diethylamino compound, and (2) b -piperidino-crotonic acid anilide is reduced as in (1) to b -piperidino butyric acid anilide. Specifications 726,864, 754,924 and 755,203 are referred to.
GB3153354A 1954-11-01 1954-11-01 Improvements in or relating to the production of -ß-substituted carboxylic acid anilides and their derivatives Expired GB781193A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3153354A GB781193A (en) 1954-11-01 1954-11-01 Improvements in or relating to the production of -ß-substituted carboxylic acid anilides and their derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3153354A GB781193A (en) 1954-11-01 1954-11-01 Improvements in or relating to the production of -ß-substituted carboxylic acid anilides and their derivatives

Publications (1)

Publication Number Publication Date
GB781193A true GB781193A (en) 1957-08-14

Family

ID=10324529

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3153354A Expired GB781193A (en) 1954-11-01 1954-11-01 Improvements in or relating to the production of -ß-substituted carboxylic acid anilides and their derivatives

Country Status (1)

Country Link
GB (1) GB781193A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3045043A (en) * 1958-08-30 1962-07-17 Hoechst Ag New gamma-hydroxy-carboxylic acid amides and process for their manufacture

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3045043A (en) * 1958-08-30 1962-07-17 Hoechst Ag New gamma-hydroxy-carboxylic acid amides and process for their manufacture

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