Morpholine → HCID 57474473, compound

Participants

Reaction Steps

A solution of compound 148 (2.35 g, 9.845 mmol) in dry CH3CN (40 mL) was treated with K2CO3 (13.6 g, 98.458 mmol), KI (16.3 g, 98.458 mmol) and morpholine (8.58 mL, 98.458 mmol) at room temperature. The resulting mixture was refluxed for overnight (15 h). The reaction was brought to room temperature and the solvent was evaporated. The mixture was diluted with water (100 mL) and extracted with ethyl acetate (2×50 mL). The combined ethyl acetate layer was washed with water (25 mL), brine (20 mL) and dried (Na2SO4). The solvent was evaporated under reduced pressure and the crude product was purified by column chromatography (EtOAC: 2M NH3 in methanol/CH2Cl2, 1:1) to obtain compound 149 (2.85 g, quantitative) as a syrup. 1H-NMR (CDCl3) δ 1.97-2.06 (m, 2H), 2.23 (t, 2H, J=6.3 Hz), 2.38 (brs, 4H), 3.75 (t, 4H, J=4.5 Hz), 4.33 (t, 2H, J=6.6 Hz), 6.59 (d, 1H, J=3.0 Hz), 7.39 (d, 1H, J=3.0 Hz), 7.64 (d, 1H, J=8.7 Hz), 8.00 (dd, 1H, J=1.8, 8.7 Hz), 8.42 (brs, 1H).

Provenance & Evidence