Abstract
Grignard reagents were prepared by the usual method from allyl, propyl, and isopropyl bromide, and cyclohexyl chloride, and their respective application to 2-dimethylaminomethylcyclohexanone gave 1-allyl-, 1-propyl-, 1-isopropyl-, and 1-cyclo-hexyl-2-dimethylaminomethylcyclohexanols. Condensation of these aminoalcohols with various kinds of aromatic acid chlorides gave a series of esters. Catalytic reduction of such an ester, p-nitrobenzoyloxy derivative, with palladium-carbon, gave p-aminobenzoyloxy derivative. Of these esters, 1-ethyl- and 1-isopropyl-1-benzoyloxy-2-dimethylaminomethylcyclohexanes showed marked analgesic activity. Application of chloroacetyl chloride and α-bromopropionyl bromide to 1-ethyl- and 1-cyclohexyl derivatives of the foregoing hexanols, respectively, yielded haloacyloxy derivatives which were condensed with dimethyl- or diethylamine to give dialkylaminoacyloxy derivatives.
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