Reaction Steps
The tert-butyl 10-(2-methylphenyl)-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate (0.53 g, 1.40 mmol) from above was treated with a solution of 4 N HCl in dioxane (10 mL) and stirred at room temperature for 3.7 hours. After the reaction mixture was concentrated in vacuo CH2Cl2 was added and the solution was concentrated in vacuo to give a green solid (475 mg) which was recrystallized from CH3OH/ethyl acetate to give 0.362 g (82%) of a light brown solid as the title compound: mp 278.5-281° C. 1H NMR (400 MHz, DMSO-d6) δ 11.20 (s, 1H), 9.40 (br s, 1H), 7.32-7.22 (m, 4H), 7.15 (d, J=7.2 Hz, 1H), 7.09-7.05 (m, 1H), 6.68 (d, J=7.1 Hz, 1H), 3.26 (m, 2H), 3.17-3.16 (m, 2H), 2.98 (m, 2H), 2.37-2.27 (m, 2H), 1.98 (s, 3H); 13C NMR (100 MHz, DMSO-d6) δ 140.9, 135.8, 135.5, 134.5, 132.7, 129.4, 129.2, 127.2, 125.3, 125.0, 120.2, 119.7, 110.0, 109.7, 45.9, 44.2, 24.3, 21.1, 19.6; IR (diffuse reflectance) 3257 (s), 2992 (s), 2946 (s,b), 2906 (s,b), 2849 (s), 2831 (s), 2801 (s), 2774 (s), 2676, 2572, 2446, 1463, 1336, 766, 744 (s) cm−1; HRMS (FAB) calcd for C19H20N2+H1 277.1704, found 277.1702. Anal. Calcd for C19H20N2.HCl.0.5EtOAc: C, 72.69; H, 6.80; N, 8.83. Found: C, 72.60; H, 6.82; N, 8.94.
