Reaction #1604345

ord-a555a33cf69948ffbcc053fc5526018e

Reaction equation

[H][H]
hydrogen
[N-]=[N+]=NCCC(CCN=[N+]=[N-])CCN=[N+]=[N-]
Tris(2-azidoethyl)methane
→
NCCC(CCN)CCN
1,1,1-tris(2-aminoethyl)methane
Yield 100.0%

Reactants

—
triamine
[H][H]
hydrogen
[N-]=[N+]=NCCC(CCN=[N+]=[N-])CCN=[N+]=[N-]
Tris(2-azidoethyl)methane
—
triazide

Reagents

[Pd]
palladium on charcoal

Solvents

CCO
ethanol

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThe reaction vessel was evacuated every 2 hours
  2. 2
    Otherto remove nitrogen
  3. 3
    Otherevolved from the reaction

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08231858B2uspto-grants-2012_07