Sodium borohydride → cis-1-Methyl-3-phenyl-4-piperidinol

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Reaction Steps

Sodium borohydride (9.46 g) is added portionwise to a solution of the compound of formula IV, (-methyl-3-phenyl-4-piperidone (94.6 g, described by A. A. Patchett and F. F. Gianuso, supra), in water-methanol 1:9 (250 ml). The mixture is stirred for 30 minutes and the methanol is evaporated. The aqueous residue is diluted with water, 6N hydrochloric acid and washed with ether. The aqueous phase is made alkaline and extracted with chloroform. The chloroform extract is evaporated and crystallized from ether to give cis-1-methyl-3-phenyl-4-piperidinol, mp 131-133° C. Anhydrous hydrogen chloride is added to the mother liquors and the precipitate is crystallized from methanol-ether to give trans-1-methyl-3-phenyl-4-piperidnol hydrochloride, mp 131-133° C.

Provenance & Evidence