N,N-Dimethylethylenediamine → N-[2-(Dimethylamino)ethyl]-4-(4-fluorophenyl)-1-piperazinecarboxamide

Participants

Reaction Steps

To a solution of 6.3 g (0.04 mole) of 1,1'-carbonyldiimidazole in 50 ml of tetrahydrofuran (THF) was added a solution of 3.4 g (0.04 mole) of unsym-dimethylethylenediamine in 75 ml of THF and the reaction mixture was stirred at ambient temperature for 1.5 hr. A solution of 7.0 g (0.04 mole) of 1-(4-fluorophenyl)piperazine in 50 ml of THF was added and the reaction mixture was heated at reflux for 20 hr. The solution was concentrated under reduced pressure and the residue was dissolved in 150 ml of benzene. The solution was washed thrice with 50 ml portions of water and once with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give an oil which solidified. After trituration with petroleum ether (30°-60° C.), the collected solid was recrystallized from isopropyl alcohol/hexane to yield 7.8 g (68%) of title compound as a crystalline, white solid, m.p. 99°-101° C.

Provenance & Evidence