1-Phenethylamine → N-(1-phenylethyl)acetamide

HRID 1282099Notes

Reaction equation

HRID 1282099 reaction equation
[C:1]1([CH:7]([NH2:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:17](OC(=O)C)(=[O:19])[CH3:18]>ClCCl>[C:1]1([CH:7]([NH:9][C:17](=[O:19])[CH3:18])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 74081-PhenethylamineHCID 7918Acetic AnhydrideHCID 8471Triethylamine

Product 1

HCID 222023N-(1-phenylethyl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-phenylethylamine (10.45 g) and triethylamine (14.4 ml) in dichloromethane (100 ml) was added dropwise acetic anhydride (9.0 ml) at room temperature. The mixture was stirred at room temperature for 5 hr. The reaction mixture was poured into ice water (200 ml) and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated. The obtained residue was left standing at room temperature for 3 hr. The obtained crude crystals were washed several times with hexane to give the title compound (14.0 g) as white crystals.

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated
  4. waitThe obtained residue was left
  5. waitstanding at room temperature for 3 hr
  6. customThe obtained crude crystals
  7. washwere washed several times with hexane

Sources & evidence

ORD record
ord-da106d333b3e424692f0a0832d3da129
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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