Sodium Iodide → n,n-Dimethyl-2-(7-nitro-1,2,4,5-tetrahydro-3h-3-benzazepin-3-yl)acetamide

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Reaction Conditions

Reaction Steps

2-(7-amino-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-N,N-dimethyl-acetamide Into a round bottom flask, 7-Nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine nitric acid salt (3.80 g, 0.0149 mol), Potassium Carbonate (6.22 g, 0.0450 mol), 2-Chloro-N,N-dimethyl-acetamide (2.30 mL, 0.00224 mol), Sodium Iodide (2.28 g, 0.0152 mol) and DMF (60 mL, 0.8 mol) were added. The mixture was heated at 60° C. overnight. The reaction was partitioned with EtOAc and washed with Water (2×). The organic was separated, washed with Brine, and dried over Sodium Sulfate. The solid was filtered and washed with EtOAc. The solvent was removed under vacuum. The product was isolated via ISCO column chromatography with DCM and Methanol as eluant (0 to 10% Methanol). The collected fractions afforded 2-(7-nitro-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-N,N-dimethyl-acetamide as an orange solid (2.31 g, 56%). MP 102-104° C. LCMS (E/I+) 278 (M+H). NMR 1H (CDCl3)-7.95 (m, 2H), 7.24 (d, 1H, J=7.76 Hz), 3.34 st, 2H), 3.12 (s, 3H), 3.03 (m, 4H), 2.97 (s, 3H), 2.76 (m, 4H).

Provenance & Evidence