HCID 17954114, compound → 460078-00-6

HRID 1774140Notes

Reaction equation

HRID 1774140 reaction equation
[N:1]([CH2:4][CH2:5][CH:6]([CH2:12][CH2:13][N:14]=[N+]=[N-])[CH2:7][CH2:8][N:9]=[N+]=[N-])=[N+]=[N-].[H][H]>C(O)C.[Pd]>[NH2:1][CH2:4][CH2:5][CH:6]([CH2:12][CH2:13][NH2:14])[CH2:7][CH2:8][NH2:9]

Participants

5

Reactant 2

HCID 17954114HCID 17954114, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 9942175460078-00-6Yield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

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).

Workup

  1. customThe reaction vessel was evacuated every 2 hours
  2. customto remove nitrogen
  3. customevolved from the reaction
  4. distillationCaution: unreduced azide could explode on distillation
  5. filtrationThe reaction was filtered through a celite pad
  6. customto remove the catalyst
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-322c15d823ce49f4b04b7ccc8dcd9472
Source dataset
uspto-grants-2016_02
Patent number
US09259496B2

Reaction notes

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