Dimethylformamide → HCID 131715617, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1,3,4,5-tetrahydro-4-(methoxyphenyl)-3-methyl-7-(trifluoromethyl)-2H-1-benzazepin-2-one (3.37 g; 9.65 mmole) in dry dimethylformamide 75 ml) was added prewashed (hexane) 50% sodium hydride (5.56 g; 11.58 mmole; 1.2 eq.) with stirring. After ~20 minutes, 1.7N (in toluene) N,N-dimethyl-2-chloroethylamine (24.0 ml; 40.8 mmole) was added, and the mixture was heated at 85° C. for four hours. The mixture was made basic with 50% sodium hydride, and extracted with ethyl acetate (three times). The combined organics were dried (magnesium sulfate) and concentrated, and the dark oily residue was placed under vacuum. The crude material was flash chromatographed (silica gel/1% methanol:dichloromethane, followed by 3% methanol:dichloromethane). The acidified (hydrogen chloride saturated ether) product weighed 1.06 g.

Provenance & Evidence