Phenethylamine → Methyl 2-(phenethylamino)acetate

HRID 1080542Notes

Reaction equation

HRID 1080542 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][CH3:15])=[O:13]>C1(C)C=CC=CC=1>[C:1]1([CH2:7][CH2:8][NH:9][CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 1001PhenethylamineHCID 60984Methyl bromoacetate

Product 1

HCID 22991956Methyl 2-(phenethylamino)acetateYield 124.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 2-phenylethylamine (9.68 g, 40 mmol) in toluene (50 mL) was added methyl bromoacetate (6.12 g, 20 mmol) dropwise at room temperature and was left stirring for 18 hours. The reaction mixture was filtered before removing the solvent in vacuo and the residue was purified by chromatography over silica gel to yield 4.8 g (61%) of the title compound as an oil. NMR (250 MHz, CDCl3) δ(1H, s), 2.92 (4H, m), 3.43 (2H, s), 3.71 (3H, s), 7.27 (5H, m).

Workup

  1. waitwas left
  2. filtrationThe reaction mixture was filtered
  3. custombefore removing the solvent in vacuo
  4. customthe residue was purified by chromatography over silica gel

Sources & evidence

ORD record
ord-88245bca604147278bfd4b05799e0143
Source dataset
uspto-grants-1996_12
Patent number
US05580896

Reaction notes

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