Dimethylformamide → N-Benzyl-N-(2,2-diethoxyethyl)-3-phenethyloxy-propanamide

Participants

Reaction Steps

3-Phenethyloxypropanoic acid (0.4 g) was dissolved in dichloromethane (10 mL) and treated with oxalyl chloride (0.35 g) and a drop of dimethylformamide at ambient temperature. The resultant solution was stirred at ambient temperature for 1 hour. The solution was then concentrated and azeotroped with dichloromethane (3×10 mL). The collected residue was dissolved in dichloromethane (5 mL) and added, portionwise, to a stirred solution of N-benzyl-2,2-diethoxy-ethanamine (0.47 g) and N-ethyl-N-isopropyl-propan-2-amine (0.6 mL), dissolved in dichloromethane (10 mL), at ambient temperature. The resultant solution was stirred at ambient temperature for 1 hour. The mixture was then poured into ethyl acetate (25 mL), washed with water (2×25 mL), washed with brine (25 mL), dried over anhydrous magnesium sulphate, filtered and concentrated to give the sub-titled compound (0.62 g) as an oil.

Provenance & Evidence