1-(2-Hydroxyethyl)piperazine → HCID 54373614, compound

Participants

Reaction Steps

5.0 g (0.036 mol) 3-(2-furyl)acrylic acid was suspended in 100 ml toluene, followed by addition of 7.9 ml (0.108 mol) thionyl chloride. The mixture was refluxed for 1 h, cooled, evaporated and the residue stripped twice with toluene. The resulting acylchloride was redissolved in 25 ml toluene and added dropwise to a solution of 4.7 g (0.036 mol) 1-piperazineethanol in 25 ml toluene and 25 ml pyridine. The reaction mixture was stirred at reflux temperature for 1 h, then cooled, diluted with toluene and washed successively with one portion of 1N sodium hydroxide and three portions of water. Evaporation in vacuo left 3.4 g of an amber oil, which was redissolved in 75 ml of tetrahydrofuran and added dropwise to a solution of 1.32 g (0.035 mol) lithium aluminium hydride in 75 ml of tetrahydrofuran. The reaction mixture was stirred at room temperature for 1 h, cooled in an ice bath and hydrolyzed by dropwise addition of water. The precipitate was filtered off and washed with tetrahydrofuran. The filtrate was concentrated in vacuo and the residue redissolved in acetonitrile. A solution of maleic acid in acetonitrile was added and the precipitate collected by filtration. Recrystallization from isopropanol gave the 1-(2-hydroxyethyl)-4-[3-(2-furyl)-2-propenyl]-piperazine as the dimaleate salt, m.p. 165°-67° C.

Provenance & Evidence