Hydrochloric Acid → 2-Phenylsulfonyl-4,5-dimethyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride

Participants

Reaction Conditions

Reaction Steps

To a solution of the product of step D (104 mg, 0.22 mmol) in chloroform (1 mL) was added 2 M HCl in diethyl ether solution (5 mL). The reaction was stirred at 0° C. for 1 h then allowed to warm to ambient temperature overnight. The mixture was concentrated in vacuo, made basic with sat. sodium bicarbonate solution and extracted with chloroform. The organic extract was dried over anhydrous sodium sulfate, concentrated in vacuo and the resulting residue purified by flash column chromatography (SiO2, 90:9.9:0.1 dichloromethane/methanol/ammonium hydroxide). The free-base was treated directly with 1.25 M HCl in methanol (2 mL) and the resulting solution concentrated in vacuo to give 2-phenylsulfonyl-4,5-dimethyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride (65 mg, 72%, AUC HPLC 98.7%) as a white solid: mp 244-248° C.; 1H NMR (CD3OD, 300 MHz): δ 8.08 (d, J=1.5 Hz, 1H), 7.90-7.98 (m, 2H), 7.49-7.63 (m, 3H), 7.38-7.43 (m, 1H), 5.26 (d, J=4.8 Hz, 1H), 4.49-4.58 (m, 1H), 3.94 (s, 3H), 3.44 (dd, J=17.1 Hz, J=4.5 Hz, 1H), 3.02 (d, J=17.4 Hz, 1H), 2.99 (s, 3H), 2.19-2.52 (m, 3H), 1.91-2.20 (m, 1H); APCI MS m/z 367 [M+H]+.

Provenance & Evidence