Methanol → 2-(7-Amino-1,2,4,5-tetrahydro-3h-3-benzazepin-3-yl)-n,n-dimethylacetamide
Reaction equation
[CH3:1][N:2]([CH3:20])[C:3](=[O:19])[CH2:4][N:5]1[CH2:11][CH2:10][C:9]2[CH:12]=[C:13]([N+:16]([O-])=O)[CH:14]=[CH:15][C:8]=2[CH2:7][CH2:6]1.CO>[Pd]>[CH3:1][N:2]([CH3:20])[C:3](=[O:19])[CH2:4][N:5]1[CH2:11][CH2:10][C:9]2[CH:12]=[C:13]([NH2:16])[CH:14]=[CH:15][C:8]=2[CH2:7][CH2:6]1Participants
4
Procedure
Into a Parr bottle, N,N-Dimethyl-2-(7-nitro-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-acetamide (2.20 g, 0.0079 mol), 10% Palladium on Carbon (50% Wet)(5:45:50, Palladium:carbon black:Water, 0.84 g, 0.0004 mol) and Methanol (50 mL, 1 mol) were added. The mixture was evacuated and charged with hydrogen at 40 psi. The reaction was shaken on the parr at 40 psi for one hour. The mixture was filtered through Celite and the Celite washed with EtOAc. The organic was evaporated under vacuum to give N,N-Dimethyl-2-(7-amino-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-acetamide as a brown gum/foam (1.96 g, 112%). LCMS (E/I+) 248 (M+H). NMR 1H (DSMO-d6)-9.90 (br. s, 2H), 7.22 (d, 1H, J=8.14 Hz), 7.06 (m, 2H), 4.36 (s, 2H), 3.66 (br. m, 4H), 3.12 (br. m, 4H), 2.96 (s, 3H), 2.91 (s, 3H).