Dimethylformamide → N-(1-Methyl-2-oxo-2-phenylethyl)-4-(phenylmethyl)-2-morpholinecarboxamide

Participants

Reaction Conditions

Reaction Steps

Oxalyl chloride (1.17 mL, 13.3 mmol) was added to the suspension of 4-(phenylmethyl)-2-morpholinecarboxylic acid (2.290 g, 8.89 mmol) and DMF (0.034 mL, 0.444 mmol) in CH2Cl2 (60 mL) at 0° C., and the resulting mixture was stirred at 25° C. for 2 hours, and then evaporated. CH2Cl2 (60 mL) was added to the resulting residue, and the resulting brown solution was added to a suspension of triethylamine (4.34 mL, 31.1 mmol) and 2-amino-1-phenyl-1-propanone (1.65 g, 8.89 mmol) in CH2Cl2 (60 mL) at 0° C. The reaction mixture was stirred at 25° C. overnight. Water (150 mL) was added, and the resulting mixture was extracted with EtOAc (3×80 mL). The organics were dried (Na2SO4), filtered, and evaporated. The resulting residue was purified by silica gel chromatography, eluting with EtOAc in PE from 20% to 50% to afford the title compound (1.3 g) as a yellow oil. LC-MS (ES) m/z=353 [M+H]+.

Provenance & Evidence