Sodium Azide → 3-(3,4-Dimethylphenoxy)propan-1-amine

HRID 1741438Notes

Reaction equation

HRID 1741438 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([CH3:13])[CH:7]=1.[N-:14]=[N+]=[N-].[Na+]>C1(C)C=CC=CC=1.[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-]>[CH3:13][C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][C:9]=1[CH3:12])[O:5][CH2:4][CH2:3][CH2:2][NH2:14]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 167880053-Chloropropyl 3,4-dimethylphenyl ether

Product 1

HCID 167827653-(3,4-Dimethylphenoxy)propan-1-amineYield 97%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

9.05 (45.6 mnol) of 1-chloro-3-(3,4-dimethylphenoxy)- propane obtained in step 1 was dissolved in 200 ml of toluene. To the resulting solution were added 14.8 g of NaN3, 2.9 g of n-Bu4NBr and 15.2 g of KI and the mixture was refluxed For 24 hours. The reaction mixture was washed with water and concentrated under a reduced pressure. The resulting residue was purified by chromatography (ethyl acetate: hexane=1:10) to obtain 9.04 g (yield 97%) of the title compound as a brown oil.

Workup

  1. temperaturethe mixture was refluxed For 24 hours
  2. washThe reaction mixture was washed with water
  3. concentrationconcentrated under a reduced pressure
  4. customThe resulting residue was purified by chromatography (ethyl acetate: hexane=1:10)

Sources & evidence

ORD record
ord-42222539caee4c66b6c68e2f9089150a
Source dataset
uspto-grants-1999_10
Patent number
US05973201

Reaction notes

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