Hydrochloric Acid → HCID 18357149, compound

Participants

Reaction Steps

To a solution of 4-phenoxybenzaldehyde (198 mg) in dichloromethane (20 ml), N-(4-pyridyl)piperazine (163 mg) and acetic acid (240 mg) were added. The mixture was stirred at ambient temperature for 30 mins, and then sodium triacetoxyborohydride (318 mg) was added in one portion. Stirring was continued at ambient temperature overnight. The reaction mixture was poured into 1M hydrochloric acid (50 ml) and washed With ethyl acetate (50 ml). The aqueous layer was made basic with 2M sodium hydroxide solution and extracted with dichloromethane (2×25 ml). The combined extracts were washed with water, dried (MgSO4) and evaporated to give a white solid which was purified by chromatography on silica gel (Mega Bond Elut column) using an increasing concentration of methanol in dichloromethane (up to 4% methanol) as eluant to give 1-(4-pyridyl)-4-(4-phenoxy-phenyl)piperazine (168 mg) as a solid: microanalysis, found: C,76.5; H,6.6; N,11.9%; C22H23N3O requires: C,76.5; H,6.7; N,12.2%; NMR: 3.2-3.45(m,8H); 3.5(s,2H); 6.8(d,2H); 6.9-7.05(m,4H); 7.1-7.2(m,1H); 7.25-7.45(m,4H); 8.1(d,2H); MS: m/z 345 (MH)+.

Provenance & Evidence