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

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Reaction Steps

The product from step C (1.22 g, 2.7 mmol) was dissolved in methanol (7 mL) and dichloromethane (5 mL) and 2N HCl in diethylether (70 mL) was added. The reaction was stirred at room temperature for 12 h, after which a precipitate formed. The mixture was diluted with diethylether and filtered providing 2-phenylsulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride (900 mg, 86%) as an off-white solid: Mpt 238-244° C. (dec.); 1H NMR (300 MHz, d6-DMSO) δ 9.69 (brs, 1H), 9.15 (brs, 1H), 8.38 (s, 1H), 7.92 (dd, J=8.0, 1.7 Hz, 2H), 7.60 (m, 5H), 5.36 (d, J=4.8 Hz, 1H), 4.47 (brs, 1H), 3.68 (s, 3H), 3.34 (dd, 1H, partially masked by solvent), 3.00 (d, J=17.2 Hz, 1H), 2.25 (m, 2H), 2.08 (t, J=9.6 Hz, 1H), 1.80 (m, 1H); ESI MS m/z 353 [M+H]+; HPLC (Method A)>99% (AUC), tR=12.02 min.

Provenance & Evidence