Methanol → 1,4-Di(n-butyl)piperazin-2-one

Reaction equation

[CH:1]([CH:3]=O)=[O:2].CO.[CH2:7]([NH:11][CH2:12][CH2:13][NH:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:8][CH2:9][CH3:10]>O1CCOCC1>[CH2:15]([N:14]1[CH2:13][CH2:12][N:11]([CH2:7][CH2:8][CH2:9][CH3:10])[CH2:3][C:1]1=[O:2])[CH2:16][CH2:17][CH3:18]

Participants

Procedure

To 10 g (69.0 mmoles) of 40 percent glyoxal and 200 ml of methanol is rapidly added 11.9 g (69.0 mmoles) of N,N'-di(n-butyl)ethylenediamine. The solution is rapidly brought to reflux and heating is maintained for 5 minutes. The dark brown solution is then allowed to cool to room temperature at which time fine white crystals precipitate from the brown oil. The oil is diluted with 100 ml of 1,4-dioxane and the solid is removed by filtration. The dioxane solution is concentrated under aspirator vacuum and distilled in a short path distillation apparatus to give 4.5 g of 1,4-di(n-butyl)piperazin-2-one in the form of a brown oil (31 percent yield).