O-Methyltyramine → N-(2-(4-Methoxyphenyl)ethyl)acetamide

HRID 1932301Notes

Reaction equation

HRID 1932301 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([CH2:7][CH2:8][NH2:9])=[CH:5][CH:4]=1.[OH-].[Na+].[C:14](Cl)(=[O:16])[CH3:15]>ClCCl>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([CH2:7][CH2:8][NH:9][C:14](=[O:16])[CH3:15])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 4657O-MethyltyramineHCID 6367Acetyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 584258N-(2-(4-Methoxyphenyl)ethyl)acetamideYield 106.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Methoxyphenethylamine (50 g, 330 mmol) was added to dichloromethane (50 ml) and then 2N sodium hydroxide solution (25 ml) was added thereto. Acetyl chloride (26 ml, 364 mmol) was slowly added at 0° C. to the reaction mixture, which was then stirred overnight. The reaction mixture was diluted with dichloromethane, washed with water and a saturated sodium chloride solution, and then extracted with dichloromethane. The organic layer was dried on anhydrous magnesium sulfate and then concentrated under reduced pressure to give 68 g of the titled compound as a white solid. The product was used in the subsequent step without further purification.

Workup

  1. washwashed with water
  2. extractiona saturated sodium chloride solution, and then extracted with dichloromethane
  3. dry with materialThe organic layer was dried on anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2d6ed314d1d44494b8694d8e45776b76
Source dataset
uspto-grants-2012_05
Patent number
US08188114B2

Reaction notes

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