Hydrochloric Acid → 4-(Benzyloxy)-1-(10-methyl-1,2,3,4,5,10-hexahydroazepino[3,4-b]indol-8-yl)pyridin-2(1H)-one hydrochloride

Participants

Reaction Steps

A solution of 4-(benzyloxy)-1-(10-methyl-1,2,3,4,5,10-hexahydroazepino[3,4-b]indol-8-yl)pyridin-2(1H)-one (30 mg, 0.075 mmol) in CH2Cl2 (1.0 mL) was treated with anhydrous 1.0 M HCl in diethyl ether (75 μL, 0.075 mmol), and the resulting solution was stirred at ambient temperature for 1 h. The solution was concentrated to dryness, diluted with H2O and lyophilized to yield the title compound (32 mg, 99%) as a yellow powder: mp 210-218° C. decomp.; 1H NMR (500 MHz, DMSO-d6) δ 9.04 (s, 2H), 7.59-7.55 (m, 2H), 7.48-7.41 (m, 5H), 7.38-7.36 (m, 1H), 6.97 (dd, J=8.5, 2.0 Hz, 1H), 6.10 (dd, J=7.5, 2.5 Hz, 1H), 5.97 (d, J=2.5 Hz, 1H), 5.15 (s, 2H), 4.53 (s, 2H), 3.74 (s, 3H), 3.49-3.47 (m, 2H), 2.97 (t, J=5.0 Hz, 2H), 1.99-1.97 (m, 2H); ESI MS m/z 400 [M+H]+; HPLC (Method A) 97.9% (AUC), tR=14.8 min.

Provenance & Evidence