Potassium Iodide → HCID 59837458, compound

Participants

Reaction Steps

A mixture of 1-{4-[4-(3-chloropropoxy)phenyl]tetrahydro-2H-pyran-4-yl}-N,N-dimethylmethanamine (200 mg, 0.7 mmol), N-methyl piperazine (87 μl, 0.79 mmol), solid sodium bicarbonate (66 mg, 0.79 mmol) and a catalytic amount of potassium iodide was heated at 50° C. in N,N-dimethylformamide (2 ml) for 18 hours. The reaction mixture was concentrated in vacuo. The residue 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 purified by flash chromatography on silica gel eluting with dichloromethane:methanol:ammonia (96:4:0.4 by volume) to provide the title compound (102 mg, 39%). 1H NMR (400 MHz, CDCl3) δ 1.84-1.91 (m, 2H), 1.95-1.99 (m, 8H), 2.07-2.11 (m, 2H), 2.30 (s, 3H), 2.40 (s, 2H), 2.42-2.59 (m, 10H), 3.54 (t, 2H), 3.72-3.78 (m, 2H), 4.00 (t, 2H), 6.86 (d, 2H), 7.20 (d, 2H). HRMS ESI+ m/z 376.2951 [MH]+.

Provenance & Evidence