Hydrochloric Acid → HCID 67238815, compound

Participants

Reaction Conditions

Reaction Steps

(2-Bromophenyl)hydrazine hydrochloride (1.8 g 8.0 mmol; Aldrich) and 6-azabicyclo[3.2.1]octan-3-one (1.0 g, 8.0 mmol; GLSyntech) were combined with a solution of HCl in acetic acid (1.0 M, 30 mL; Aldrich) and stirred at 100° C. for 18 hours in a sealed tube. The reaction mixture was concentrated under vacuum and partitioned between sodium carbonate (1.0 M, 500 mL) and chloroform (2×300 mL). The combined organic extracts were dried over sodium sulfate and concentrated in vacuo. The crude product was purified by reverse-phase HPLC [Waters XBridge™ RP18 column, 5 μm, 50×100 mm, flow rate 100 mL/minute, 40-100% 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 (400 MHz, methanol-d4) δ ppm 1.89-1.94 (m, 1H), 2.05 (ddd, J=10.8, 6.0, 4.3 Hz, 1H), 2.81 (dd, J=16.8, 2.4 Hz, 1H), 3.03 (dd, J=9.6, 1.4 Hz, 1H), 3.09-3.17 (m, 2H), 3.42 (t, J=3.7 Hz, 1H), 3.88 (dt, J=5.7, 2.8 Hz, 1H), 6.87 (t, J=7.6 Hz, 1H), 7.14 (dd, J=7.6, 0.9 Hz, 1H), 7.41 (dd, J=7.9, 0.9 Hz, 1H); MS (ESI+) m/z 277/279 (M+H)+.

Provenance & Evidence