N-phenethyl-N-propyl-3,4-dimethoxyphenethylamine → 4-{2-[(2-Phenylethyl)(propyl)amino]ethyl}benzene-1,2-diol

HRID 46776Notes

Reaction equation

HRID 46776 reaction equation
[CH2:1]([N:9]([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21]C)=[C:17]([O:23]C)[CH:16]=1)[CH2:10][CH2:11][CH3:12])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>Br>[CH2:1]([N:9]([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([OH:23])[CH:16]=1)[CH2:10][CH2:11][CH3:12])[CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 1

HCID 12411034N-phenethyl-N-propyl-3,4-dimethoxyphenethylamine

Product 1

HCID 30486884-{2-[(2-Phenylethyl)(propyl)amino]ethyl}benzene-1,2-diolYield 94.5%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A solution of 9.37 g of the product of Step B in 90 ml of 48% hydrobromic acid was refluxed for 3 hours under a nitrogen atmosphere and was then evaporated to dryness. The residue was taken up in 50 ml of ammonium hydroxide solution and the solution was extracted with methylene chloride. The organic extracts were washed with water, dried over magnesium sulfate, filtered and evaporated to dryness to obtain 8.1 g of N-phenethyl-N-propyl-3,4-dihydroxyphenethylamine in the form of a reddish oil.

Workup

  1. customwas then evaporated to dryness
  2. extractionthe solution was extracted with methylene chloride
  3. washThe organic extracts were washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-e7aca4c10bec4b2c820e51a605cbb214
Source dataset
uspto-grants-1979_11
Patent number
US04175136

Reaction notes

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