Water → HCID 59807097, compound

Participants

Reaction Steps

A suspension of 7-nitro-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one (490 mg, 2.38 mmol), 2-chloro-N,N-dimethylethanamine hydrochloride (685 mg, 4.75 mmol) and potassium carbonate (1.97 g, 14.28 mmol) in 15 mL DMF was stirred at room temperature for 1 day. A TLC analysis indicated that the starting material is still present. The mixture was treated with 2-chloro-N,N-dimethylethanamine hydrochloride (685 mg, 4.75 mmol) and potassium carbonate (1.97 g, 14.28 mmol) followed by 5 mL DMF and stirring was continued at room temperature for 18 hours. After this time, the mixture was poured into 50 mL H2O then extracted with 2×100 mL of ethyl acetate. The combined organic fractions were washed with brine, dried over Na2SO4, filtered and concentrated to give a dark residue. The residue was subjected to flash chromatography on silica gel using 2-5% 2M NH3 in MeOH/CH2Cl2 to give a yellow viscous oil (412 mg, 62.4%). 1H-NMR (DMSO-d6) δ 8.21-8.15 (m, 2H), 7.67 (d, J=8.7 Hz, 1H), 3.92-3.90 (m, 2H), 2.87-2.83 (m, 2H), 2.27 (t, J=6.3 Hz, 2H), 2.21-2.11 (m, 4H), 2.03 (s, 6H). MS (EI): 278.1 (M+1).

Provenance & Evidence