Dimethylformamide → HCID 66989829, compound

Participants

Reaction Steps

N,N-Dimethylformamide (0.010 mL) and oxalyl chloride (0.21 mL) were sequentially added to a methylene chloride (3.0 mL) suspension of 2-(benzyloxy)-5-(piperidin-1-yl)benzoic acid (0.56 g), followed by stirring at room temperature for 1 hour and 20 minutes. Under ice-cooling, the reaction mixture was added to a solution mixture of 2-amino-4-chlorobenzonitrile (0.23 g) in methylene chloride (3.0 mL) and pyridine (0.30 mL), followed by stirring at room temperature for 2 hours and 30 minutes. The solvent was evaporated under reduced pressure, and a 10% aqueous solution of citric acid and chloroform were added to the residue. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 95-85% hexane/ethyl acetate] to obtain 2-(benzyloxy)-N-(5-chloro-2-cyanophenyl)-5-(piperidin-1-yl)benzamide as a yellow solid.

Provenance & Evidence