N,N-Dimethyl-4-nitrobenzylamine → Benzenemethanamine, 4-amino-N,N-dimethyl-

HRID 1387773Notes

Reaction equation

HRID 1387773 reaction equation
[CH3:1][N:2]([CH3:13])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][CH:5]=1>C(O)C>[NH2:10][C:7]1[CH:6]=[CH:5][C:4]([CH2:3][N:2]([CH3:13])[CH3:1])=[CH:9][CH:8]=1

Participants

3

Reactant 1

HCID 278498N,N-Dimethyl-4-nitrobenzylamine

Product 1

HCID 308051Benzenemethanamine, 4-amino-N,N-dimethyl-Yield 50.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In ethanol (100 ml) was dissolved dimethyl-4-nitro-benzylamine (20.7 g), and to the mixture was added dried 10% palladium on carbon (1.00 g). Under hydrogen atmosphere, the mixture was stirred at room temperature under atmospheric pressure for 20 hours. The palladium was filtered off, and the filtrate was concentrated. The residue was separated and purified with column chromatography (ethyl acetate) to give 4-aminobenzyldimethylamine (8.75 g) as pale yellow oil.

Workup

  1. additionto the mixture was added
  2. dry with materialdried 10% palladium on carbon (1.00 g)
  3. filtrationThe palladium was filtered off
  4. concentrationthe filtrate was concentrated
  5. customThe residue was separated
  6. custompurified with column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-c69cb77f347e4e3086ffc3ff6416f4f8
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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