Hydrochloric Acid → 2-(4-Aminomethylphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole dihydrochloride

Participants

Reaction Steps

The product of step A was subjected to Boc-deprotection with 2 M HCl in diethyl ether following the procedure of Example 28, step B. The crude material was purified by flash column chromatography (SiO2, 80:18:2 chloroform/methanol/ammonium hydroxide). The free base was treated with 1.25 M HCl in methanol (0.5 mL). The solution was concentrated in vacuo and the residue lyophilized to give 2-(4-Aminomethylphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole dihydrochloride (13 mg, 76%, AUC HPLC 97.0%) as an off-white solid: mp 237-239° C.; 1H NMR (DMSO-d6, 300 MHz) δ 9.72 (br s, 1H), 9.26 (br s, 1H), 8.50 (br s, 3H), 8.38 (s, 1H), 7.97 (d, J=8.1 Hz, 2H), 7.58-7.74 (m, 4H), 5.34 (br s, 1H), 4.46 (br s, 1H), 4.07 (br s, 2H), 3.67 (s, 3H), 3.39-3.46 (m, 1H), 3.00 (d, J=17.4 Hz, 1H), 2.19-2.39 (m, 2H), 2.04-2.15 (m, 1H), 1.71-1.88 (m, 1H); ESI MS m/z 382 [M+H]+.

Provenance & Evidence