Methyl chloroformate → HCID 11792901, compound

Participants

Reaction Steps

A mixture of N-benzyl-N-methyl-2-[5-chloro-1-(4-fluorophenyl)-3-1H-indolyl]ethylamine (14a) (13.7 g, 0.026 mol), methyl chloroformate (2.9 g, 0.031), K2 CO3 (4.2 g, 0.031) and 1,1,1-trichloroethane (150 mL) was heated at reflux for 2 h and the precipitates was filtered off. Evaporation of the solvents afforded crude N-methyl-N-methoxycarbonyl-2-[5-chloro-1-(4-fluorophenyl)-3-1H-indolyl]ethylamine (12.2 g) as an oil. A mixture of the crude N-methoxycarbonyl-2-[5-chloro-1-(4-fluorophenyl)-3-1H-indolyl]ethylamine (12.2 g, 0.034) and 47% hydrobromic acid (150 mL) was heated at reflux for 14 h. The reaction mixture was poured into ice, made alkaline with concentrated NaOH and extracted with diethyl ether (2×200 mL). The combined organic phases were washed with brine and dried (Na2 SO4). Evaporation of the solvents afforded pure title compound as an oil (7.9 g, 52%) which was crystalized as its maleate from ethyl acetate: mp 171°-173° C. (ethyl acetate); 1H NMR (DMSO-d6) δ 2.65 (s, 3 H), 3.05-3.20 (m, 2 H), 3.20-3.30 (m, 2 H), 6.05 (s, 2 H), 7.20 (broad d, 1 H), 7.45 (t, 2 H), 7.50 (s, 1 H), 7.60 (dd, 2 H), 7.65 (s, 1 H), 7.80 (broad s, 1 H); MS (m/z) 303 (MH+), 237 (82) 236 (100). Anal. (C17H16FClN2.C4H4O4) C, H, N.

Provenance & Evidence