Compounds of the alpha-Prodine Type. V. Preparation of 1-Substituted Homologs and Analogs of 1-Benzoylethyl-4-Phenyl-4-Piperidinol and Their Esters. Reduction of Keto Esters to the Corresponding Hydroxy Esters.
Technical rept. Jan 63-Jun 70,
EDGEWOOD ARSENAL ABERDEEN PROVING GROUND MD
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The preparation and use of a number of Mannich bases and the corresponding methiodides for the synthesis of 1-substituted-4-phenyl-4-piperidinols and their ester hydrochlorides is described. Substituents in the 1-position included phenyl substituted benzoylethyl, 2-benzoylpropyl, 2-furoylethyl, 2-thenoylethyl, 2-2-dibenzothenoyl, and 3-2-thienyl-2-propenyl groups. Monoesters were prepared by acylating the desired piperidinol with acyl halides of 2 to 4 carbon atoms diesters were prepared by acylating 2 moles of the desired piperidinol with 1 mole of diacyl halide of up to 6 carbon atoms. An unusual diester was prepared by acylation of 1,4-bis3-4-pehnyl-4-hydroxy-1-piperidinopropionylbenzene with 2 moles of a monoacyl halide. A successful, reliable method was developed for the catalytic reduction of keto ester hydrochlorides to the corresponding hydroxy ester hydrochlorides.
- Organic Chemistry