m-Chloroperbenzoic acid → N-[(2E)-4-[4-(2,3-Dichlorophenyl)-1-oxido-1-piperazinyl]-2-buten-1-yl]-4-(2-pyridinyl)benzamide

Participants

Reaction Steps

A solution of PG01037, see U.S. 2006/0106030 (288 mg, 0.60 mmol) in 10 mL dichloromethane was treated at 0° C. with meta-chloroperbenzoic acid (0.16 g, 77%, 0.72 mmol). After stirring for 16 h at room temperature, the reaction mixture was successively washed with saturated sodium bicarbonate solution, H2O and brine and dried with sodium sulphate. The volatiles were removed in vacuo and the residue was purified by preparative thin layer chromatography. Yield: 93 mg (32%). Mp. (hydrochloride): foam. 1H NMR (CD3OD): δ 3.23-3.29 (m, 4H), 3.50-3.61 (m, 4H), 3.99 (d, J 6.5, 1H), 4.13 (d, J 4.6, 1H), 6.04-6.18 (m, 2H), 7.18 (dd, J 7.8, 3.9, 1H), 7.24-7.28 (m, 2H), 7.40 (m, 1H), 7.91-7.93 (m, 2H), 7.99 (d, J 8.4, 2H), 8.06 (d, J 8.7, 2H), 8.64 (dt, J 4.8, 1.2, 1H). 13C NMR (CDCl3): δ 41.0, 45.5, 63.5, 72.0, 119.3, 120.0, 121.6, 123.1, 125.4, 127.0, 127.3, 127.7, 128.0, 133.8, 134.6, 137.8, 137.9, 142.2, 149.3, 150.1, 156.4, 168.3. Anal. (C26H26Cl2N4O2:2HCl.0.5H2O) C, H, N.

Provenance & Evidence