4-[2-(3,4-Dichlorophenyl)-[1,3]dioxolan-2-yl]piperidine → N-(1-{4-[2-(3,4-dichlorophenyl)-[1,3]dioxolan-2-yl]piperidin-1-yl-methyl}-2-methylpropyl)-4-methylbenzamide

Participants

Reaction Steps

A solution of 4-[2-(3,4-dichlorophenyl)-[1,3]dioxolan-2-yl]piperidine (0.21 g, 0.7 mmol), N-p-toluoyl valinaldehyde (0. 17g, 0.764 mmol), sodium triactetoxy-borohydride (0.22 g, 1.04 mmol) in methylene chloride (20 mL) was stirred overnight under argon. After concentrating the reaction mixture, the residue was stirred with ethyl acetate and dilute aqueous potassium carbonate solution. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. The crude was flash chromatographed on flash silica gel with 1% methanol/methylene chloride (containing 1% ammonia) to give N-(1-{4-[2-(3,4-dichlorophenyl)-[1,3 ]dioxolan-2-yl]piperidin-1-yl-methyl}-2-methylpropyl)-4-methylbenzamide (0.187g, 0.366 mmoles).

Provenance & Evidence