1-(2-Hydroxyethyl)piperazine → 1-(2-Hydroxyethyl)-4-[(2-methoxyphenyl)methyl]piperazine

Participants

Reaction Steps

2-Methoxybenzyl chloride (16 g) and 1-(2-hydroxyethyl)piperazine (13 g) in ethanol (50 ml) were heated under reflux for 4 hours. The solvent was removed under vacuum and the resulting oil was passed through a pad of silica gel eluting with 10% methanol-ammonia in dichloromethane to give 1-(2-hydroxyethyl)-4-[(2-methoxyphenyl)methyl]piperazine as a colourless oil (80%), 13C nmr (CDCl3) 157.4, 130.3, 127.8, 125.2, 119.8, 110.0, 59.5, 57.6, 55.2, 54.8, 52.7 and 52.4 ppm. This material (15 g) was treated at 0° C. with thionyl chloride (15 ml). The mixture was then heated at reflux for 2 hours. Toluene was added and the mixture was evaporated under reduced pressure. The resulting solid was collected and washed thoroughly to give the dihydrochloride of the title compound as a white solid, m.p. 276°-279° C. (dec.).

Provenance & Evidence