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

HRID 482457Notes

Reaction equation

HRID 482457 reaction equation
[CH3:1][O:2][CH2:3][C:4](Cl)=[O:5].[C:7]1([CH2:13][CH2:14][NH2:15])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(C(C)C)C(C)C)C>ClCCl>[CH3:1][O:2][CH2:3][C:4]([NH:15][CH2:14][CH2:13][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5]

Participants

5

Reactant 3

HCID 1001PhenethylamineHCID 81531DiisopropylethylamineHCID 96623Methoxyacetyl chloride

Product 1

HCID 149486162-Methoxy-N-(2-phenylethyl)acetamideYield 85.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methoxyacetyl chloride (19.57 g, 0.18 mol) was added over 10 minutes to a stirred, ice-cooled solution of 2-phenylethylamine (21.85 g, 0.18 mol) and N-ethyldiisopropylamine (23.26 g, 0.18 mol) in dichloromethane (200 ml). After 2 hours at room temperature, the solvent was removed under reduced pressure and the residue partitioned between ether and water. The organic phase was washed successively with 1M aqueous citric acid solution, water, saturated aqueous sodium bicarbonate solution and water, dried (MgSO4) and evaporated under reduced pressure to provide the required product (29.65 g) as an oil, Rf 0.32 (SS 2), which was used without further purification in the next step.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customthe residue partitioned between ether and water
  3. washThe organic phase was washed successively with 1M aqueous citric acid solution, water, saturated aqueous sodium bicarbonate solution and water
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-11980ad520f9419aa488e101525578a2
Source dataset
uspto-grants-1998_08
Patent number
US05798352

Reaction notes

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