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

HRID 2215367

Reaction equation

HRID 2215367 reaction equation
[CH3:1][C:2]([N+:13]([O-])=O)([CH3:12])[CH2:3][NH:4][CH2:5][C:6]([N+:9]([O-])=O)([CH3:8])[CH3:7]>CO.[Ni]>[CH3:8][C:6]([NH2:9])([CH3:7])[CH2:5][NH:4][CH2:3][C:2]([NH2:13])([CH3:1])[CH3:12]

Participants

4

Reactant 1

HCID 21951119Di-(2-nitroisobutyl)amine

Product 1

HCID 226845Bis(2-amino-2-methylpropyl)amine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

490 g (2.23 mol) of bis-(2-methyl-2-nitropropyl)amine from reaction 1) are dissolved in 1200 ml of methanol and transferred into an autoclave. 60 g of Raney Ni are added. The autoclave is closed and purged with nitrogen. Then, hydrogen is added until the hydrogen pressure is 50 bars. That pressure is maintained at room temperature for 8 hours and, subsequently, the reaction mixture is heated to 50° C. at the same pressure. The catalyst is then separated off by filtration and the mixture is distilled under vacuum (100° C./33.3 mbar). A colourless oil is recovered (Boiling point: 110° C./5 mbar).

Workup

  1. customThe autoclave is closed
  2. custompurged with nitrogen
  3. additionThen, hydrogen is added until the hydrogen pressure
  4. temperaturesubsequently, the reaction mixture is heated to 50° C. at the same pressure
  5. customThe catalyst is then separated off by filtration
  6. distillationthe mixture is distilled under vacuum (100° C./33.3 mbar)
  7. customA colourless oil is recovered (Boiling point: 110° C./5 mbar)

Sources & evidence

ORD record
ord-9b5c2fefa2bd4c11bc70d34013b34e69
Source dataset
uspto-grants-2006_09
Patent number
US07109259B2

Linked notes

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