Phenethylamine → N-(2-phenylethyl)acetamide

HRID 2105711Notes

Reaction equation

HRID 2105711 reaction equation
[C:1]1([CH2:7][CH2:8][NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:10](OC(=O)C)(=[O:12])[CH3:11]>N1C=CC=CC=1>[C:10]([NH:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:12])[CH3:11]

Participants

4

Reactant 2

HCID 1001PhenethylamineHCID 7918Acetic Anhydride

Product 1

HCID 70143N-(2-phenylethyl)acetamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A commercially available solution of 2-phenylethylamine (2 ml, 15.8 mmol) in pyridine (5 ml) is added with acetic anhydride (2 eq., 3 ml) and the solution is stirred at room temperature for 12 hours. The solvent is evaporated off under reduced pressure and the residue is taken up with water (40 ml) and the aqueous phase is extracted with EtOAc (4×25 ml). The organic extracts are pooled, anhydrified over Na2SO4 and evaporated under reduced pressure. The residue is crystallised from petroleum ether to give compound 28 as white solid (2.56 g, quantitative yield).

Workup

  1. customThe solvent is evaporated off under reduced pressure
  2. extractionthe aqueous phase is extracted with EtOAc (4×25 ml)
  3. customevaporated under reduced pressure
  4. customThe residue is crystallised from petroleum ether

Sources & evidence

ORD record
ord-d8b88a7b587e42e9bf39d0d3c08e77c5
Source dataset
uspto-grants-2009_08
Patent number
US07579378B2

Reaction notes

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