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

HRID 1277020Notes

Reaction equation

HRID 1277020 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-nitrobenzylamine (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-aminobenzyl-dimethylamine (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-1d2e6ee0f4794d238ec2135eb0b2091f
Source dataset
uspto-grants-2000_12
Patent number
US06166006

Reaction notes

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