Hydrochloric Acid → 2-(3-Fluorophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride

Participants

Reaction Steps

The product of step A (105 mg, 0.22 mmol) was treated with a solution of 4 M HCl in dioxane (1.5 mL). After 1.5 h the mixture was concentrated in vacuo and the residue partitioned with saturated sodium bicarbonate solution and chloroform. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography (SiO2, 90:9:1 chloroform/methanol/ammonium hydroxide) to give 2-(3-fluorophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride (45 mg, 50%, AUC HPLC 98.8%) as a white solid: mp 240-245° C.; 1H NMR (DMSO-d6, 300 MHz) δ 8.20-8.70 (m, 3H), 7.74-7.81 (m, 2H), 7.59-7.71 (m, 3H), 7.45-7.55 (m, 1H), 5.15-5.24 (m, 1H), 4.31-4.43 (m, 1H), 3.66 (s, 3H), 3.21-3.39 (m, 1H), 2.92 (d, J=16.8 Hz, 1H), 2.12-2.29 (m, 2H), 1.96-2.09 (m, 1H), 1.66-1.80 (m, 1H); ESI MS m/z 371 [M+H]+.

Provenance & Evidence