Diethylamine → Methyl 2-(2-(benzyloxy)-5-(2-(diethylamino)ethoxy)benzamido)-4-phenylbenzoate

Participants

Reaction Steps

Potassium carbonate (0.15 g) and diethylamine (0.11 mL) were added to an acetone (2.0 mL) solution of methyl 2-(2-(benzyloxy)-5-(2-bromoethoxy)benzamido)-4-phenylbenzoate (0.20 g), followed by heating to reflux for 4 hour and 30 minutes. The reaction mixture was cooled to room temperature, and then potassium carbonate (0.049 g) and diethylamine (0.037 mL) were added thereto, followed by heating to reflux for 1 hour. The reaction mixture was cooled to room temperature, and then potassium carbonate (0.049 g) and diethylamine (0.037 mL) were added thereto, followed by heating to reflux for 1 hour and 15 minutes. The reaction mixture was cooled to room temperature, and then potassium carbonate (0.049 g) and diethylamine (0.037 mL) were added thereto, followed by heating to reflux for 5 hours and 30 minutes. The reaction mixture was cooled to room temperature, and water, a saturated aqueous solution of sodium bicarbonate, and ethyl acetate were added thereto. 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: 100-97% chloroform/methanol] to obtain 0.15 g of methyl 2-(2-(benzyloxy)-5-(2-(diethylamino)ethoxy)benzamido)-4-phenylbenzoate.

Provenance & Evidence