Water → ethyl N-[4-(2-hydroxyethyl)phenyl]-N-methylaminoacetate

HRID 275987Notes

Reaction equation

HRID 275987 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][CH:5]=1.[C:17](=O)([O-])[O-].[K+].[K+].CI.O>CN(C)C=O>[OH:1][CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH3:17])=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 10537054ethyl N-[4-(2-hydroxyethyl)phenyl]aminoacetate

Product 1

HCID 10561854ethyl N-[4-(2-hydroxyethyl)phenyl]-N-methylaminoacetateYield 67.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl N-[4-(2-hydroxyethyl)phenyl]-aminoacetate (1.15 g) in N,N-dimethylformamide (10 ml) were added potassium carbonate (1.17 g) and methyl iodide (420 μl), and the mixture was stirred for 9 hours at room temperature. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was removed in vacuo. Purification of the residue by flash column chromatography on silica gel (eluent: dichloromethane/diethyl ether=10/1) gave ethyl N-[4-(2-hydroxyethyl)phenyl]-N-methylaminoacetate (820 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed in vacuo
  5. customPurification of the residue by flash column chromatography on silica gel (eluent: dichloromethane/diethyl ether=10/1)

Sources & evidence

ORD record
ord-fa34c717b8194f6ebeb23365d2839fc2
Source dataset
uspto-grants-2002_03
Patent number
US06353025B1

Reaction notes

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