Triethylamine → 2-[4-[3-Chloro-4-(hydroxymethyl)phenyl]-1-piperazinyl]-1-(2-furanyl)-1-propanone

Participants

Reaction Steps

At ~25°, a solution of 2-chloro-4-(1-piperaziny)-benzenemethanol 3.0 g, 13.2 mmole) in 30 ml of tetrahydrofuran and 4 ml of triethylamine was added during five minutes to a solution of 3-chloro-1-(2-furanyl)-1-propanone (2.8 g. 13.3 mmole based on 75% purity). The mixture was stirred at 25° for one hour (a white precipitate formed) and was then heated under reflux for one half hour. The mixture was then filtered and the filtrate was evaporated at reduced pressure (<40°) to give an orange, heavy oil. The oil was triturated at 25° first with petroleum ether (30°-60°; two times, 50 ml) and then with diethyl ether. The orange-brown solid was collected, washed with a little diethyl ether, recrystallized from 25 ml of toluene, and finally triturated with diethyl ether (two times, 20 ml) and dried to give 3.10 g (67%), mp 95°-98° (Table 3).

Provenance & Evidence