Abstract
A series of 1-alkyl (or aryl)-2-dialkylaminocyclohexanones (III to X) were prepared by the reaction of the Grignard reagents of methyl, ethyl, propyl, butyl, benzyl, and phenyl halides with 2-dialkylaminocyclohexanones (I and II) obtained from 2-halocyclohexanone and dialkylamines. (X) gives 1-phenyl-1-benzoyloxy-2-dimethylaminocyclohexane hydrochloride (XI) on the application of benzoyl chloride but (IV), (VI), and (VII) only afford their own hydrochlorides. Treatment of (X) with formic acid or dry hydrogen chloride gas affords 1-phenyl-2-dimethylaminocyclohex-1- or -6-ene (XII). The use of sodium as the condensation agent in the reaction of 2-ethoxycarbonylcylohexanone and dialkylamino-ethyl chloride gives 2-β-dialkylaminoethyl-2-ethoxycarbonylcyclohexanones (XI and XII). Further treatment of these with barium hydroxide to 2-β-dialkyl-aminoethylcyclohexanones (XIII and XIV) and application of the Grignard reagents of methyl, ethyl, butyl, and phenyl halides afford the corresponding 2-β-dialkyl-aminoethyl-1-alkyl (or aryl) cyclohexanols (XV to XXI).
