Hydrochloric Acid → N-(1-(3-Bromophenyl)ethyl)-2-nitro-5-(piperazin-1-yl)benzenamine hydrochloride

Participants

Reaction Steps

A mixture of tert-butyl 4-(3-(1-(3-bromophenyl)ethylamino)-4-nitrophenyl)piperazine-1-carboxylate (0.45 g, 0.9 mmol), 2N HCl in ether (10 mL, 20.0 mmol) and dichloromethane (5 mL) was stirred for 18 h and concentrated in vacuo. The residue was dissolved in dichloromethane; this solution was washed with aqueous NaHCO3 solution, dried over Na2SO4 and concentrated in vacuo. The yellow solid residue was dissolved in dichloromethane (0.5 mL) and reacted with 1N HCl in ether (1 mL). The resulting precipitates were collected by vacuum filtration, washed with ether and air dried to yield the title compounds as a yellow solid (0.13 g, 33%). 1H NMR (400 MHz, CDCl3): δ 8.71 (d, 1 H), 8.05 (d, 1 H), 7.50 (s, 1 H), 7.39 (m, 1 H), 7.23 (m, 2 H), 6.19 (dd, 1 H), 5.60 (d, 1 H), 4.53 (m, 1 H), 3.21 (m, 2 H), 3.13 (m, 2 H), 2.88 (m, 4 H), 1.63 (d, 3 H). MS (ESI) m/z: Calculated: 404; Observed: 405 (M+H+).

Provenance & Evidence