Potassium Iodide → HCID 66758616, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(4-chloro-phenyl)-3-(S)-methyl-piperazine (0.56 g, 2.6 mmol) in isopropanol (20 mL) was added 2,6-lutidine (0.305 mL, 2.6 mmol) and catalytic potassium iodide. This mixture was heated to 80° C., and then treated with 2-[5-(3-bromo-propylidene)-5,11-dihydro-10-oxa-1-aza-dibenzo[a,d]cyclohepten-7-yl]-propan-2-ol (0.64 g, 1.7 mmol), added in portions over 2 h. The solution was then stirred at 80° C. for an additional 20 h. The reaction was concentrated in vacuo and purified by flash chromatography (100% dichloromethane to 2% methanol/dichloromethane) to yield the title compound (0.151 g, 18%). 1H-NMR (CDCl3) δ: 1.0 (3H, d), 1.57 (6H, s), 1.79 (s, 1H), 2.25–2.52 (7H, m), 2.66–2.69 (1H, m), 2.98–3.12 (2H, m), 3.68–3.73 (1H, m), 5.32 (2H, br s), 6.17 (1H, t), 6.82 (3H, d), 7.18–7.31 (4H, m), 7.44 (1H, d), 7.56–7.60 (1H, m), 8.50 (1H, dd). ESI-MS m/z: 504 (M), UV retention time: 1.49 min.

Provenance & Evidence