Potassium Iodide → HCID 66758692, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(4-chloro-phenyl)-N-piperidin-4-yl-acetamide (0.2 g, 0.8 mmol) in isopropanol (6.0 mL) was added 2,6-lutidine (0.095 mL, 0.8 mmol) and catalytic potassium iodide. This mixture was heated to 80° C. and treated with 2-[5-(3-bromo-propylidene)-5,11-dihydro-10-oxa-1-aza-dibenzo[a,d]cyclohepten-7-yl]-propan-2-ol (0.15 g, 0.4 mmol) in portions over 2 h. The solution was then stirred at 80° C. for an additional 18 h. The reaction mixture was concentrated in vacuo, then purified by flash chromatography on silica gel (gradient elution from 95% ethyl acetate/5% methanol to 90% ethyl acetate/20% methanol) to yield the title compound. 1H-NMR (CDCL3) δ: 1.15–1.50 (4H, m), 1.60 (6H,s), 1.80–2.85 (8H, m), 3.50 (2H, s), 3.70–3.90 (1H, m), 5.20 (2H, br s), 6.05(1H, t), 6.80 (1H, d), 7.20–7.40 (7H, m) 7.60 (1H,dd), 8.50 (1H,dd). ESI-MS m/z: 546 (M+1), UV retention time: 1.24 min.

Provenance & Evidence