Reaction #619262

Reaction equation

hydrogen

Tris(2-azidoethyl)methane

→

tris(2-aminoethyl)methane

Yield 100.0%

Solvents

ethanol

Conditions

Workup

1. 1
   OtherThe reaction vessel was evacuated every 2 hours
2. 2
   Otherto remove nitrogen
3. 3
   Otherevolved from the reaction
4. 4
   workup.DISTILLATIONCaution: unreduced azide could explode on distillation
5. 5
   FiltrationThe reaction was filtered through a celite pad
6. 6
   Otherto remove the catalyst
7. 7
   Concentrationconcentrated in vacuo

Procedure

Tris(2-azidoethyl)methane (15.06 g, 0.0676 mol), (assuming 100% yield from previous reaction) in ethanol (200 ml) was treated with 10% palladium on charcoal (2 g, 50% water) and hydrogenated for 12 h. The reaction vessel was evacuated every 2 hours to remove nitrogen evolved from the reaction and refilled with hydrogen. A sample was taken for NMR analysis to confirm complete conversion of the triazide to the triamine. Caution: unreduced azide could explode on distillation. The reaction was filtered through a celite pad to remove the catalyst and concentrated in vacuo to give tris(2-aminoethyl)methane as an oil. This was further purified by Kugelrohr distillation bp. 180-200° C. at 0.4 mm/Hg to give a colourless oil (8.1 g, 82.7% overall yield from the triol).

Source