Potassium Carbonate → HCID 59837354, compound

Participants

Reaction Steps

Tosylmethyl isocyanide (370 mg, 1.89 mmol) was added to a solution of 4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbaldehyde (500 mg, 1.58 mmol) and potassium carbonate (652 mg, 4.73 mmol) in methanol (7 ml). The reaction mixture was heated at reflux for 3 hours. The reaction mixture was partitioned between ethyl acetate (2×75 ml) and water (20 ml). The organic layers were combined, dried over sodium sulphate, filtered and concentrated in vacuo. The crude product was taken up in 2N hydrochloric acid (3 ml) and stirred at room temperature for 1.5 hours. The mixture was then partitioned between aqueous sodium carbonate and dichloromethane (2×75 ml). The combined organic layers were dried over sodium sulphate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:ammonia (95:5:0.5 by volume) to provide the title compound (12 mg, 2%). 1H NMR (400 MHz, CD3OD) δ 1.81-1.85 (m, 4H), 1.97-2.02 (m, 2H), 2.25-2.31 (m, 2H), 2.38-2.43 (m, 2H), 2.60-2.63 (m, 4H), 2.69 (t, 2H), 3.61 (t, 2H), 3.78-3.83 (m, 2H), 4.01 (t, 2H), 6.87 (d, 2H), 6.98 (s, 1H), 7.22 (d, 2H), 8.09 (s, 1H). LRMS APCI+ m/z 357 [MH]+.

Provenance & Evidence