Methanol → Tris(3-aminopropyl)amine

Participants

Reaction Steps

Tris(2-cyanoethyl)amine (2.80 g, 15.9 mmol) was dissolved in BH3.THF and refluxed under nitrogen for 48 h. MeOH (ca. 20 cm3) was added dropwise to the solution with vigorous stirring until no more gas was evolved. The solution was evaporated to dryness under vacuum and the resultant white precipitate refluxed in 6M hydrochloric acid (250 cm3) until the solution cleared. The hydrochloric acid was removed under reduced pressure and the resultant solid was dissolved in the minimum amount of water. The solution was divided up into two portions. Each portion was applied to a basic ion exchange column (DOWEX ion exchange resin, 20-50 mesh) and the amine eluted in water (ca. 250 cm3). The water was removed under reduced pressure to yield Tris(3-aminopropyl)amine (1.78 g, 59%) as a clear oil.

Provenance & Evidence