Phenethylamine → HCID 11031025, compound

HRID 2305236Notes

Reaction equation

HRID 2305236 reaction equation
[C:1]1([CH2:7][CH2:8][NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O>[CH2:8]([NH:9][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 1001PhenethylamineHCID 7748Ethyl bromoacetateHCID 8471Triethylamine

Product 1

HCID 11031025HCID 11031025, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-phenylethylamine (3.0 g, 24.8 mmol) in DMF (30 ml) was added ethyl bromoacetate (3.0 ml, 27.3 mmol) at 5° C. Then triethylamine (4.15 ml, 29.8 mmol) was added thereto at the same temperature. After stirring the resulting mixture at room temperature for 18 hours, the reaction mixture was diluted with EtOAc, washed with water and brine successively, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography (methylene chloride:MeOH, 20:1) to give ethyl phenethylaminoacetate (1.87 g, 37%) as an oil.

Workup

  1. washwashed with water and brine successively
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was purified by silica gel column chromatography (methylene chloride:MeOH, 20:1)

Sources & evidence

ORD record
ord-99fc2d1e40d24e4ab81e0f0b6c6b0f89
Source dataset
uspto-grants-2002_08
Patent number
US06437146B1

Reaction notes

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