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
  • C07D295/16—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 acylated on ring nitrogen atoms
  • C07D295/18—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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
  • C07D295/182—Radicals derived from carboxylic acids
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C231/00—Preparation of carboxylic acid amides
  • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines

Definitions

• the invention relates to a process for the preparation of hydroxyalkanecarboxamides of the general formula I.
• n represents an integer from 1 to 20 and
• R ⁇ and R 2 each represent alkyl groups with a maximum of 8 carbon atoms or together represent an alkylene group with 4 to 8 carbon atoms, optionally interrupted by an oxygen atom or a nitrogen atom, from hydroxyalkanecarboxylic acids of the general formula II
• R ⁇ and R 2 have the abovementioned meaning, which is characterized in that the hydroxyalkanecarboxylic acid is heated under reflux with 10 to 30 moles of acetyl chloride per mole of acid in a one-pot reaction, the excess acetyl chloride is distilled off after acetylation, and the residue is 1.5 to 5 moles of thionyl chloride per mole of acid are heated under reflux, the thionyl chloride is removed by distillation after the formation of acid chloride, the residue is dissolved in a dialkyl ether having 4 to 8 carbon atoms, the solution obtained is cooled to 0 ° C. to 10 ° C.
• the invention relates to the preparation of hydroxyalkanecarboxamides of the general formula I ## STR1 ## in which the group
• R3 and R4 independently represent a hydrogen atom or a methyl group and X represents a methylene group an oxygen atom or an N-CH3 group.
• hydroxyalkanecarboxamides of the general formula I are known to be valuable intermediates and / or pharmacologically active substances.
• R5 represents a hydrogen atom or an alkyl group, valuable intermediates for
• the process according to the invention is carried out in such a way that the hydroxyalkane carboxylic acid is dissolved or suspended in 10 to 30 moles of acetyl chloride per mole of acid and the reaction mixture is heated under reflux. After acetylation has taken place (recognizable by thin-layer chromatographic analysis, or by the fact that no more hydrogen chloride is produced), the excess acetyl chloride is distilled off, care being taken to remove the acetyl chloride as completely as possible by applying a vacuum.
• dialkyl ether having 4 to 8 carbon atoms.
• Suitable dialkyl ethers are, for example, diethyl ether, diisopropyl ether, dibutyl ether or, in particular, methyl tert-butyl ether.
• the ethereal solution of the acid chloride is then introduced into a preferably stirred and, if appropriate, mixed with the same ether, cooled to 0 ° C. to 10 ° C., aqueous solution of preferably 2 to 5 mol of amine per mol of acid used, so that the reaction temperature is 10 ° C does not exceed.
• the reaction mixture is then left to stand at room temperature for a further 20-60 minutes to complete the reaction, and an excess of aqueous or aqueous / alcoholic sodium hydroxide solution is added and the mixture is stirred at room temperature for 20-60 minutes.
• the reaction mixture is prepared in a customary manner, for example by separating the organic phase, washing it, concentrating it and cleaning the residue by recrystallization.
• a g of ⁇ -hydroxyalkanoic acid are suspended in b ml of acetyl chloride and heated under reflux and stirring for 30 minutes. Then the acetyl chloride is distilled off in vacuo, c ml of thionyl chloride is added to the residue and the mixture is heated at 60 ° C. for one hour. Then the thionyl chloride is distilled off in vacuo and the residue is dissolved in d ml of methyl tert-butyl ether.
• e ml of 40% aqueous dimethylamine solution are mixed with f ml of methyl tert-butyl ether and cooled to 0 ° C. with stirring.
• the ethereal acid chloride solution is then added dropwise to this mixture such that the reaction temperature does not exceed 10 ° C., stirring is continued for 30 minutes at room temperature, and a solution of mercury sodium hydroxide in a mixture of i ml methanol and k ml water is added to the reaction mixture and stirred for a further 30 minutes at room temperature.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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• 1992
  • 1992-05-07 DE DE19924214895 patent/DE4214895A1/de not_active Withdrawn
• 1993
  • 1993-05-05 WO PCT/DE1993/000413 patent/WO1993022278A1/de not_active Application Discontinuation
  • 1993-05-05 JP JP5518842A patent/JPH07506819A/ja active Pending
  • 1993-05-05 EP EP93911742A patent/EP0639177A1/de not_active Withdrawn
  • 1993-05-05 HU HU9401335A patent/HUT68198A/hu unknown
  • 1993-05-05 AU AU42594/93A patent/AU4259493A/en not_active Abandoned
  • 1993-05-05 CA CA002127292A patent/CA2127292A1/en not_active Abandoned
• 1994
  • 1994-11-03 FI FI945181A patent/FI945181A/fi not_active Application Discontinuation
  • 1994-11-07 NO NO944238A patent/NO944238D0/no unknown

Non-Patent Citations (1)

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