Methanol → Tris(3-aminopropyl)amine

HRID 1859271Notes

Reaction equation

HRID 1859271 reaction equation
[C:1]([CH2:3][CH2:4][N:5]([CH2:10][CH2:11][C:12]#[N:13])[CH2:6][CH2:7][C:8]#[N:9])#[N:2].CO>B.C1COCC1>[NH2:2][CH2:1][CH2:3][CH2:4][N:5]([CH2:10][CH2:11][CH2:12][NH2:13])[CH2:6][CH2:7][CH2:8][NH2:9]

Participants

4

Reactant 2

HCID 887MethanolHCID 82028Propanenitrile, 3,3',3''-nitrilotris-

Product 1

HCID 547030Tris(3-aminopropyl)amineYield 59.4%

Reagents, catalysts & solvents 1

HCID 2723981Borane;tetrahydrofuranSolvent

Procedure

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.

Workup

  1. temperaturerefluxed under nitrogen for 48 h
  2. customThe solution was evaporated to dryness under vacuum
  3. temperaturethe resultant white precipitate refluxed in 6M hydrochloric acid (250 cm3) until the solution
  4. customThe hydrochloric acid was removed under reduced pressure
  5. dissolutionthe resultant solid was dissolved in the minimum amount of water
  6. washthe amine eluted in water (ca. 250 cm3)
  7. customThe water was removed under reduced pressure

Sources & evidence

ORD record
ord-4c77a6eb7ac0420fb20777fa0ad5705f
Source dataset
uspto-grants-2000_11
Patent number
US06153775

Reaction notes

Loading…