Ethylenediamine → 2-(Furan-3-yl)piperazine

Participants

Reaction Steps

To a solution of 6.25 ml of n-butyl lithium in ether at -78° C., under argon, was added 1.46 g of 3-bromofuran. The reaction was stirred at -78° C. for 30 minutes and then a solution of 1.13 g of N-acetyl-N,-O-dimethylhydroxyamine in ether was added. The mixture was stirred for an additional hour at -78° C., then raised to room temperature and quenched with dilute acid. The mixture was extracted several times with ether. The extracts were combined, dried and evaporated, giving 8.88 g of solid. A solution of this solid in 200 ml of dioxane was added to a mixture of 9.99 g of selenium dioxide, 1.62 ml of water and 200 ml of dioxane, which had been heated at 55° C. until a solution formed. This mixture was refluxed for 4 hours, then cooled and filtered through hydrous magnesium silicate. The filtrate was concentrated and purified by silica gel chromatography, eluting with hexane:ethyl acetate (4:1), giving 5.1 g of solid. To a solution of 4.544 g of this solid in 100 ml of ethanol at.0° C., under argon, was added dropwise a solution of 1.8 g of ethylene diamine in 20 ml of ethanol, followed by 10 ml of dioxane. This mixture was stirred at room temperature for 3-hours, then cooled to 0° C. and 2.42 g of sodium borohydride was added. This mixture was stirred at 0° C. for 2 hours, then quenched with water and evaporated. The residue was recrystallized from dichloromethane, giving 3.35 g of 3-(3-furanyl)piperazine.

Provenance & Evidence