2-Bromophenylhydrazine hydrochloride → 4-Bromo-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride

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A mixture of 2-bromophenylhydrazine hydrochloride (4.44 g, 19.81 mmol, Aldrich) and t-butyl 3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate (4.48 g, 19.89 mmol, Chem-Impex) in 1 M HCl/acetic acid was stirred at 20-25° C. for 20 hours, and then heated at 65-70° C. for 48 hours. The mixture was cooled to room temperature and concentrated under vacuum. The residue was heated to boiling in absolute ethanol (25 mL) and the suspension was stirred at room temperature for 2 hours, then filtered. The solid was washed with cold ethanol and dried under vacuum to provide the title compound: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.74-1.86 (m, 1H), 2.07 (t, J=9.7 Hz, 1H), 2.15-2.32 (m, 2H), 2.88 (d, J=17.4 Hz, 1H), 3.35-3.49 (m, 1H), 4.41 (s, 1H), 5.16 (d, J=4.4 Hz, 1H), 6.98 (t, J=7.7 Hz, 1H), 7.25-7.37 (m, 1H), 7.58 (d, J=7.9 Hz, 1H), 8.63-9.49 (m, 1H), 11.37 (s, 1H); MS (DCI/NH3) m/z 277/279 (M+H)+.

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