Methanol → 2-(7-Amino-1,2,4,5-tetrahydro-3h-3-benzazepin-3-yl)-n,n-dimethylacetamide

Participants

Reaction Steps

N,N-Dimethyl-2-(7-nitro-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-acetamide (150 mg, 0.541 mmol) was placed in methanol (10.0 mL, 247 mmol) and 10% palladium on carbon (50% Wet) (5:45:50, palladium:carbon black:water, 15.0 mg) was added. The reaction was hydrogenated at 30 psi. for 1 hour, filtered through Celite, and then concentrated under reduced pressure to obtain 2-(7-Amino-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-N,N-dimethyl-acetamide as an orange solid (134 mg, 100%). LCMS (m/e) 248 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 6.88 (d, 1H, J=7.5 Hz), 6.50-6.44 (m, 2H), 3.54 (bs, 2H), 3.28 (s, 2H), 3.16 (s, 3H), 2.98 (s, 3H), 2.870-2.81 (m, 4H), 2.71-2.62 (m, 4H).

Provenance & Evidence