Potassium Carbonate → N-phenethyl-N-propyl-3-methoxyphenethylamine

HRID 66127Notes

Reaction equation

HRID 66127 reaction equation
[CH2:1](I)[CH2:2][CH3:3].C(=O)([O-])[O-].[K+].[K+].[CH2:11]([NH:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=1)[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CC(C)=O>[CH2:11]([N:19]([CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=1)[CH2:1][CH2:2][CH3:3])[CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 12477997N-phenethyl-3-methoxyphenethylamine

Product 1

HCID 12478003N-phenethyl-N-propyl-3-methoxyphenethylamine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1.1 ml of propyl iodide and 1.1 g of potassium carbonate were added to a solution of 1.1 g of the product of Step A in 15 ml of acetone and the mixture was refluxed with stirring for 5 hours. The acetone was distilled under reduced pressure and 50 ml of water were added thereto. The mixture was extracted 3 times with 20 ml of methylene chloride and the combined organic phases were washed with 70 ml of aqueous sodium chloride solution. The organic phases were dried over magnesium sulfate, filtered and evaporated to dryness under reduced pressure to obtain 1.25 g of N-phenethyl-N-propyl-3-methoxyphenethylamine in the form of an orange oil.

Workup

  1. temperaturethe mixture was refluxed
  2. distillationThe acetone was distilled under reduced pressure and 50 ml of water
  3. additionwere added
  4. extractionThe mixture was extracted 3 times with 20 ml of methylene chloride
  5. washthe combined organic phases were washed with 70 ml of aqueous sodium chloride solution
  6. dry with materialThe organic phases were dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-513f67831ac641ba96946d2e51567ccf
Source dataset
uspto-grants-1978_12
Patent number
US04130658

Reaction notes

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