Morpholine → HCID 59837379, compound

Participants

Reaction Steps

A mixture of 1-{4-[4-(3-chloropropoxy)phenyl]tetrahydro-2H-pyran-4-yl}-N,N-dimethylmethanamine (100 mg, 0.32 mmol), morpholine (100 mg, 1.1 mmol) and potassium carbonate (100 mg, 0.72 mmol) was heated at reflux in acetonitrile (5 ml) for 8 hours. Further morpholine (100 mg, 1.1 mmol) and potassium carbonate (100 mg, 0.72 mmol) were added and the reaction mixture heated at reflux for 6 hours. The reaction mixture was concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:ammonia (90:10:1 by volume) to provide the title compound (61 mg, 52%). 1H NMR (400 MHz, CD3OD) δ 0.81-0.87 (m, 2H), 1.04-2.01 (m, 8H), 2.13-2.18 (m, 2H), 2.48-2.50 (m, 6H), 2.56 (t, 2H), 3.50 (t, 2H), 3.68-3.77 (m, 6H), 4.03 (t, 2H), 6.90 (d, 2H), 7.27 (d, 2H). HRMS ESI+ m/z 363.2635 [MH]+.

Provenance & Evidence