Sulfuric Acid → 7-(benzyloxy)-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

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Under nitrogen, (2-(benzyloxy)phenyl)hydrazine (214 mg, 1.0 mmol, International Publication No. WO2009001129) was mixed with the product of Example 1A (139 mg, 1.0 mmol) and sulfuric acid (0.2 mL, 3.76 mmol; J. T. Baker) in dry dioxane (10 mL). Then the mixture was heated to 80° C. and stirred for 16 hours in a sealed tube. The mixture was concentrated and basified with 1.0 M NaOH and then extracted with ethyl acetate (3×20 mL). The organic phase was concentrated and purified by reverse-phase HPLC [Waters XBridge™ RP18 column, 5 μm, 30×100 mm, flow rate 40 mL/minute, 20-99% gradient of methanol in buffer (0.1 M aqueous ammonium bicarbonate, adjusted to pH 10 with ammonium hydroxide)] to afford the title compound: 1H NMR (300 MHz, methanol-d4) δ ppm 2.01-2.13 (m, 4 H), 3.01-3.13 (m, 3 H), 3.17-3.28 (m, 2 H), 4.22 (s, 2 H), 5.21 (s, 2 H), 6.66 (dd, J=7, 2 Hz, 1 H), 6.83-6.93 (m, 2 H), 7.28-7.41 (m, 3 H), 7.48-7.55 (m, 2 H); MS (DCI/NH3) m/z 319 (M+H)+.

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