Di-(2-nitroisobutyl)amine → Bis(2-amino-2-methylpropyl)amine

HRID 571594Notes

Reaction equation

HRID 571594 reaction equation
[N+:1]([C:4]([CH3:15])([CH3:14])[CH2:5][NH:6][CH2:7][C:8]([N+:11]([O-])=O)([CH3:10])[CH3:9])([O-])=O.[H][H]>[Ni].C(O)C>[NH2:11][C:8]([CH3:10])([CH3:9])[CH2:7][NH:6][CH2:5][C:4]([NH2:1])([CH3:14])[CH3:15]

Participants

5

Reactant 2

HCID 21951119Di-(2-nitroisobutyl)amineHCID 178418361HCID 178418361, compound3×

Product 1

HCID 226845Bis(2-amino-2-methylpropyl)amineYield 52%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Into a 2 L pressure reactor, 21.17 g (0.0965 mol) of compound III was placed along with 600 mL of ethanol (90%). Approximately 3 g of Raney Nickel was added and the bomb was pressurized to 90 PSI with hydrogen (99.9%). The solution was stirred and intermittently repressurized with hydrogen. Over the course of 5 days, 105 PSI (0.406 mol) of hydrogen were consumed. The bomb was then depressurized and the solution filtered through celite to remove the catalyst. The filtrate was evaporated under vacuum to remove all solvent and then was vacuum distilled at room temperature and a pressure of 50 mtorr. Purified product weighed 8.031 g, giving a yield of 52%. Purity was checked by NMR, with a singlet at 2.26 ppm and a singlet at 0.96 ppm.

Workup

  1. filtrationthe solution filtered through celite
  2. customto remove the catalyst
  3. customThe filtrate was evaporated under vacuum
  4. customto remove all solvent
  5. distillationdistilled at room temperature
  6. customgiving a yield of 52%

Sources & evidence

ORD record
ord-5fd45ad2e1874859bcba9fbdb89c970a
Source dataset
uspto-grants-2015_05
Patent number
US09029189B2

Reaction notes

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