Methanol → 2-Phenylpropylamine

HRID 1712113Notes

Reaction equation

HRID 1712113 reaction equation
[N+:1]([CH2:4][CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:6])([O-])=O.CO>[Pd]>[NH2:1][CH2:4][CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:6]

Participants

4

Reactant 2

HCID 887MethanolHCID 11400973(1-Methyl-2-nitroethyl)benzene

Product 1

HCID 113982-PhenylpropylamineYield 96%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Under argon atmosphere, 121 mg of optically active 1-nitro-2-phenylpropane (732 μmol) were dissolved in 5 mol of dry methanol and 50 mg of palladium on charcoal (10%) were added thereto. The obtained suspension was vigorously stirred under hydrogen atmosphere for 24 hours. The mixture was filtered and the solid was washed with methanol. The solvent was evaporated and the residue was dissolved in 2 ml of benzene. The solvent was evaporated to give 95 mg of an optically active 1-amino-2-phenylpropane as a colorless oil (703 μmol).

Workup

  1. filtrationThe mixture was filtered
  2. washthe solid was washed with methanol
  3. customThe solvent was evaporated
  4. dissolutionthe residue was dissolved in 2 ml of benzene
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-36216d137f0d4a7397397ccfed7dcd97
Source dataset
uspto-grants-2010_09
Patent number
US07790900B2

Reaction notes

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