Phenethylamine → 2-Methoxy-N-(2-phenylethyl)acetamide

HRID 275899Notes

Reaction equation

HRID 275899 reaction equation
[CH2:1]([NH2:9])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1(N=C=NC2CCCCC2)CCCCC1.[CH3:25][O:26][CH2:27][C:28](O)=[O:29]>ClCCl>[C:3]1([CH2:2][CH2:1][NH:9][C:28](=[O:29])[CH2:27][O:26][CH3:25])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 1001PhenethylamineHCID 10868DicyclohexylcarbodiimideHCID 12251Methoxyacetic Acid

Product 1

HCID 149486162-Methoxy-N-(2-phenylethyl)acetamideYield 45.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Phenethylamine(11.6 ml, 92.1 mmol) was added dropwise to a solution of dicyclohexylcarbodiimide(19 g, 92.1 mmol), methoxyacetic acid(8.3 g, 92.1 mmol) in dichloromethane(50 ml) at room temperature. After addition was completed, the reaction mixture was stirred for 1 hour at room temperature and the resulting solid was filtered. The filtrate was washed with aqueous hydrochloric acid solution, and the organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure to afford 8.15 g of the titled compound.

Workup

  1. additionAfter addition
  2. filtrationthe resulting solid was filtered
  3. washThe filtrate was washed with aqueous hydrochloric acid solution
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2588df02169e40679139006184cf03df
Source dataset
uspto-grants-2002_03
Patent number
US06352993B1

Reaction notes

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