Hydrogen Bromide → HCID 58907750, compound

Participants

Reaction Steps

8-(3-Methoxy-phenyl)-3-aza-bicyclo[3.2.1]octane (162 mg, 0.638 mmol) was dissolved in glacial HOAc (2 mL), charged with hydrobromic acid (48%, 2 mL), then heated to a gentle reflux overnight (or until judged complete by TLC). The reaction was carefully poured onto 1N NaOH (30 mL); pH 14 was achieved. The product was extracted with n-butanol/toluene (3/1, 6×6 mL), washed with saturated aqueous NaCl solution (1×10 mL), dried over Na2SO4, and concentrated to yield a yellow semi-solid. To this was added 2.5N HCl/EtOAc (4 mL), then azeotroped from MeOH (2×10 mL) to yield the title compound as a yellow solid (130 mg, 85%). (TLC 10% MeOH/CH2Cl2, (NH3) Rf 0.10); 1H NMR (400 MHz, CD3OD, HCl salt) δ 7.05 (t, J=7.9 Hz, 1H), 6.67 (d, J=7.9 Hz, 1H), 6.54 (s, 1H), 6.53 (dd, J=7.9, 2.3 Hz, 1H), 3.27 (ddd, J=3.3, 3.3, 1.7 Hz, 1H), 2.85 (d, J=12.9 Hz, 2H), 2.80 (dd, J=12.9, 3.1 Hz, 2H), 2.39 (br s, 2H), 1.67 (m, 2H), 1.57 (m, 2H); GCMS m/z 203 (M)+; LCMS m/z 204.3 (M+1)+.

Provenance & Evidence