Hydrochloric Acid → HCID 67085735, compound

Participants

Reaction Steps

To a solution of the product of step A (0.30 g, 0.56 mmol) in ethanol (20 mL) was added concentrated HCl (8.0 mL). The reaction mixture was stirred at ambient temperature overnight then concentrated in vacuo. The residue was purified by semi-preparative HPLC. The free base was dissolved in methanol and treated with concentrated HCl then concentrated to dryness in vacuo to give 2-[(3-phenyl)-phenyl]sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride (98 mg, 38%, AUC HPLC 97.7%) as a light brown solid: mp 230-235° C. dec; 1H NMR (CDCl3, 300 MHz) δ 9.71 (s, 1H), 9.12 (s, 1H), 8.45 (d, J=1.2 Hz, 1H), 8.15 (t, J=1.2 Hz, 1H), 7.89-7.94 (m, 2H), 7.75 (dd, J=6.6, 1.2 Hz, 1H), 7.63-7.71 (m, 4H), 7.48-7.53 (m, 2H), 7.40-7.46 (m, 1H), 5.36 (d, J=3.0 Hz, 1H), 4.45 (br s, 1H), 3.67 (s, 3H), 3.37 (dd, J=12.9, 3.3 Hz, 1H), 2.99 (d, J=12.9 Hz, 1H), 2.23-2.31 (m, 2H), 1.99-2.11 (m, 1H), 1.74-1.81 (m, 1H); ESI MS m/z 429 [M+H]+.

Provenance & Evidence