1-(2-Methoxyphenyl)piperazine → 3-[4-(2-Methoxyphenyl)piperazinyl]-2-phenylpropionic acid

Participants

Reaction Steps

1-(2-Methoxyphenyl)piperazine (22.6 g, 0.118 mol) and atropic acid (174 g, 0.118 mol) in ethanol (300 ml) were heated under reflux for 18 hours, cooled to room temperature, and evaporated in vacuo. The solid was triturated with acetone (3×100 ml) to give a first crop of α-[1-[4-(2-methoxyphenyl)piperazinyl]methyl]phenyl acetic acid (13.8 g) as white crystals. The filtrate was evaporated in vacuo to give an oil which slowly crystallized over a one month period of time. The solid was triturated with acetone (200 ml) to give a second crop of the hemihydrate of the α-[1-[4-(2-methoxyphenyl)piperazinyl]methyl]phenylacetic acid (9.01 g) as white crystals, m.p. 160°-163° C.

Provenance & Evidence