Diisopropylamine → N-(4-n-butoxyphenyl)-N-methyl-2-(1-benzyl-4-hydroxypiperidin-4-yl)acetamide

Participants

Reaction Steps

A solution of 4′-n-butoxy-N-methylacetanilide (0.34 g) in anhydrous tetrahydrofuran (1.5 mL) was added to a solution of lithium diisopropylamide prepared from diisopropylamine (0.22 mL) and n-butyl lithium (1.58M hexane solution; 1.07 mL) in an anhydrous tetrahydrofuran (1.6 mL) under cooling with ice-water, and the mixture was stirred for 30 minutes. A solution of 1-benzylpiperidin-4-one (0.32 g) in anhydrous tetrahydrofuran solution (1.5 mL) was added to thereto under cooling with ice-water, followed by additional stirring for 30 minutes. After increasing the temperature to room temperature, water was added to the mixture and extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled off. The titled compound (0.33 g) was obtained by recrystallization of the residue from hexane.

Provenance & Evidence