Dimethylformamide → N-(2,2-Diethyloxyethyl)-N-phenethyl-3-phenethyloxy-propanamide

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Reaction Steps

3-Phenethyloxypropanoic acid (0.34 g) was dissolved in dichloromethane (20 mL) and treated with oxalyl chloride (0.32 g) and a drop of dimethylformamide at ambient temperature. The resultant solution was stirred at ambient temperature for 2 hours. The solution was then concentrated and azeotroped with dichloromethane (2×20 mL). The collected residue was dissolved in dichloromethane and added, portionwise, to a stirred solution of 2,2-diethoxy-N-phenethyl-ethanamine (0.41 g) and triethylamine (0.6 mL), dissolved in dichloromethane (20 mL), at ambient temperature. The resultant solution was stirred at ambient temperature for 2 hours. The mixture was then concentrated, taken up in ethyl acetate (50 mL), washed with water (2×25 mL), washed with brine (50 mL), dried over anhydrous magnesium sulphate, filtered and concentrated to give the sub-titled compound (0.53 g) as a viscous oil.

Provenance & Evidence