Methyl iodide → N-(2-(4-Methoxyphenyl)ethyl)acetamide

HRID 275898

Reaction equation

HRID 275898 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].IC.[OH:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][NH:18][C:19](=[O:21])[CH3:20])=[CH:12][CH:11]=1>C(O)C.C(OCC)(=O)C>[CH3:1][O:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][NH:18][C:19](=[O:21])[CH3:20])=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 121051N-Acetyltyramine

Product 1

HCID 584258N-(2-(4-Methoxyphenyl)ethyl)acetamideYield 61%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate (3.5 g, 25.5 mol) and iodomethane(2.0 ml, 31.9 mmol) was added to a solution of N-(4-hydroxyphenylethyl)acetamide (4.4 g, 24.6 mmol) in ethanol(2.4 ml), which was then refluxed for 12 hours. The resulting solid was filtered and washed with ethanol. The filtrate was concentrated to give oily residue, which was diluted with ethyl acetate and washed with water. The separated organic layer was concentrated and the resulting solid was suspended in ethylether, filtered, and dried to give 2.9 g of the titled compound.

Workup

  1. temperaturewas then refluxed for 12 hours
  2. filtrationThe resulting solid was filtered
  3. washwashed with ethanol
  4. concentrationThe filtrate was concentrated
  5. customto give oily residue, which
  6. washwashed with water
  7. concentrationThe separated organic layer was concentrated
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-5c11490e8aac4d3482257346829179eb
Source dataset
uspto-grants-2002_03
Patent number
US06352993B1

Linked notes

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