Dimethylformamide → N-[2-(3-Chlorophenyl)-2-oxoethyl]-4-(phenylmethyl)-2-morpholinecarboxamide

Participants

Reaction Conditions

Reaction Steps

Oxalyl chloride (1.32 mL, 15.03 mmol) was added to the suspension of 4-(phenylmethyl)-2-morpholinecarboxylic acid (2.218 g, 10.02 mmol) and DMF (0.155 mL, 2.005 mmol) in CH2Cl2 (100 mL) at 0° C. in 10 minutes, and the resulting mixture was stirred at 25° C. for 2 hours. The mixture was concentrated, and the resulting residue was dissolved in CH2Cl2 (100 mL) and triethylamine (3.07 mL, 22.05 mmol). 2-Amino-1-(3-chlorophenyl)ethanone (1.7 g, 10.02 mmol) was added to the brown solution at 0° C., and the reaction mixture was stirred at 25° C. for 3 hours. Water (150 mL) was added to the reaction mixture, and the aqueous mixture was extracted with EtOAc (3×100 mL). The combined organic layers were dried (Na2SO4), filtered, and evaporated. The resulting residue was purified by silica gel chromatography using as eluent 50% EtOAc in petroleum ether to afford the title compound (800 mg) as a pale yellow solid. LC-MS (ES) m/z=373 [M+H]+.

Provenance & Evidence