Acetic Acid → HCID 21963247, compound

Participants

Reaction Steps

4-[2-(4-Benzo[d]isothiazol-3-yl-piperazin-1-yl)-ethyl]-phenylamine (338.4 mg, 1.0 mmol) was reacted at reflux for 30 min with o-phthaldialdehyde (147.5 mg, 1.1 mmol) and a catalytic amount of acetic acid (57 μL, 0.1 mmol) in acetonitrile (100 mL) to give the title compound. The product obtained was purified by elution through a flash column (silica gel 40, 230–400 mesh, 100:8:1, CH2Cl:EtOH:NH4OH) to give a yellow crystalline material, yield=245 mg (53.9%). mp 175.9° C. MS (APCI): 455 [M+H]+. 1H-NMR (dmso-d6, δ): 2.59 (m, 2H) 2.66 (m, 4H) 2.77 (m, 2H) 3.43 (m, 4H) 4.98 (s, 2H) 7.30 (d, J=8.79 Hz, 2H) 7.40 (dd, J=8.67, 7.45 Hz, 1H) 7.52 (m, 2H) 7.64 (m, 2H) 7.77 (m, 3H) 8.03 (d, J=9.28 Hz, 2H).

Provenance & Evidence