Tetrahydrofuran → HCID 12515637, compound

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Reaction Steps

The solution of 4 parts of 1-(2,2-diphenylethyl)-4-piperidinone in 50 parts by volume of tetrahydrofuran is cooled in an ice bath with stirring. To this solution is added 9.8 parts by volume of 2.2 M solution of isopropylmagnesium chloride in ether, and the resultant mixture is stirred for about 75 minutes at 0° C., and then quenched with the careful addition of 50 parts by volume of 10% ammonium chloride solution. The organic layer is separated and the aqueous phase is extracted with additional ethyl ether. The combined organic fractions are dried and concentrated to give yellow oil. This oil is chromatographed on silica gel using 10% acetone-methylene chloride mixture as the eluant to give yellow glass which upon trituration with heptane and recrystallization from a minimal amount of 95% ethanol affords 1-(2,2-diphenylethyl)-3-[1-(2,2-diphenylethyl)-4-hydroxypiperidin-4-yl]-4-piperidinone, melting at about 125°-127° C. This compound is represented by the following structural formula ##STR37##

Provenance & Evidence