Water → HCID 18357053, compound

Participants

Reaction Steps

A solution of N-(4-pyridyl)piperazine (9.78 g), 4-fluorobenzonitrile (7.26 g) and powdered potassium carbonate(10 g) was stirred at 100° C. in DMSO (100 ml) overnight. The solution was poured into water (500 ml) to give a precipitate which was filtered and washed with water. The crude solid was dried in a vacuum oven overnight then dissolved in dichloromethane and purified by flash chromatography on alumina (ICN Alumina N 32-63) using an increasing concentration of ethyl acetate in dichloromethane (up to 100% ethyl acetate) as eluant. This gave a solid which was recrystallised from a mixture of ethyl acetate/isohexane to give 1-(4-cyanophenyl)-4-(4-pyridyl)piperazine (7.5 g) as a solid, m.p.157-158° C.; microanalysis. found: C,72.7; H,6.1; N,21.0%; C16H16N4 requires: C,72.7; H,6.1; N,21.2%; NMR: 3.45-3.55(bs, 8H), 6.8-6.9(d, 2H), 7.0-7.1(d, 2H), 7.55-7.65(d, 2H), 8.1-8.2(d, 2H); MS: m/z 265 (MH)+.

Provenance & Evidence