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

HRID 1289473Notes

Reaction equation

HRID 1289473 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-102ba2f79ea94cceac80589e7f61595c
Source dataset
uspto-grants-1998_05
Patent number
US05750520

Reaction notes

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