3-(3,4-Dimethylphenoxy)propylazide → 3-(3,4-Dimethylphenoxy)propan-1-amine

HRID 1741439Notes

Reaction equation

HRID 1741439 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[CH3:15])[O:5][CH2:6][CH2:7][CH2:8][N:9]=[N+]=[N-].[H][H]>C(OCC)(=O)C.[Pd]>[CH3:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[CH3:15])[O:5][CH2:6][CH2:7][CH2:8][NH2:9]

Participants

5

Reactant 2

HCID 218358373-(3,4-Dimethylphenoxy)propylazideHCID 178418361HCID 178418361, compound

Product 1

HCID 167827653-(3,4-Dimethylphenoxy)propan-1-amineYield 48%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

6.20 g (30.2 mmol) of 3-(3,4-dimethylphenoxy)propylazide obtained in step 2 was dissolved in 150 ml of ethyl acetate and then 4.99 g of 5% Pd/C was added thereto to carry out a hydrogenation reaction at a hydrogen pressure of 40 psi for 30 minutes. The reaction mixture was passed through a Celite™ layer to remove Pd/C, concentrated under a reduced pressure to produce a residue, which was distilled under a reduced pressure to obtain 2.59 g (yield 48%) of the title compound as a colorless oil.

Workup

  1. customto remove Pd/C
  2. concentrationconcentrated under a reduced pressure
  3. customto produce a residue, which
  4. distillationwas distilled under a reduced pressure

Sources & evidence

ORD record
ord-b660e26f51f140408653144cb589466b
Source dataset
uspto-grants-1999_10
Patent number
US05973201

Reaction notes

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