Water → (2-Amino-benzylamino)-acetic acid methyl ester

HRID 472752Notes

Reaction equation

HRID 472752 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH2:9].Br[CH2:11][C:12]([O:14][CH2:15]C)=[O:13].O>O1CCOCC1>[CH3:15][O:14][C:12](=[O:13])[CH2:11][NH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH2:9]

Participants

5

Reactant 3

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 1780962-(Aminomethyl)aniline

Product 1

HCID 65440269(2-Amino-benzylamino)-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

2-Aminomethyl-phenylamine (1.54 g, 10.1 mmol) and TEA (3.06 ml, 20.2 mmol) are refluxed in 1,4-dioxane. A solution of ethyl bromoacetate (1.12 ml, 10.1 mmol) in 1,4-dioxane (5 ml) is added slowly over 1 hour resulting in a precipitate. The reaction mixture is stirred at reflux for 2 hours. The reaction mixture is cooled to RT, treated with water and extracted with EtOAc, the organic phase is dried over MgSO4, filtered and is concentrated in vacuo. Purification by flash column chromatography on silica, eluting with DCM:MeOH (40:1) affords the title compound; [M+H]+ 195.

Workup

  1. customresulting in a precipitate
  2. temperatureat reflux for 2 hours
  3. extractionextracted with EtOAc
  4. dry with materialthe organic phase is dried over MgSO4
  5. filtrationfiltered
  6. concentrationis concentrated in vacuo
  7. customPurification by flash column chromatography on silica
  8. washeluting with DCM:MeOH (40:1)

Sources & evidence

ORD record
ord-3886cd3db847427b806635279db4bdd8
Source dataset
uspto-grants-2014_01
Patent number
US08633211B2

Reaction notes

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