Acetic Acid → HCID 18542682, compound

Participants

Reaction Steps

To a solution of 3-[3-[N-[4-(1-t-butoxycarbonylpiperidin-4-yloxy)phenyl]amino]-1-(E)-propenyl]benzonitrile (1000 mg) and glycolaldehyde dimer (277 mg) in dichloromethane (20 ml) were added acetic acid (0.13 ml) and sodium cyanoborohydride (72 mg) in an ice bath. The mixture was stirred at the same temperature for 5 hours and then at room temperature for 4 hours. After addition of water, the reaction mixture was extracted with ethyl acetate. The extract was washed with brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and the filtrate concentrated in vacuo. The residue was purified by chromatography on a silica gel column using hexane/ethyl acetate=4/3 as an eluant to give the desired compound (1100 mg, yield 50%) as a pale yellow oil.

Provenance & Evidence