Ethyl bromoacetate → ethyl N-[4-(2-hydroxyethyl)phenyl]aminoacetate

HRID 275982Notes

Reaction equation

HRID 275982 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].C(NCC)C>CN(C)C=O>[OH:8][CH2:7][CH2:6][C:5]1[CH:9]=[CH:10][C:2]([NH:1][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 8021DiethylamineHCID 11430Potassium CarbonateHCID 669044-Aminophenethyl alcohol

Product 1

HCID 10537054ethyl N-[4-(2-hydroxyethyl)phenyl]aminoacetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-aminophenethyl alcohol (25 g) in N,N-dimethylformamide (500 ml) were added potassium carbonate (30 g) and ethyl bromoacetate (24 ml), and the mixture was stirred for 16 hours at room temperature. Diethylamine (38 ml) was added to the reaction mixture, and the resulting mixture was stirred for 1 hour. The insoluble material was filtered off and the filtrate was concentrated in vacuo. To the residue was added diethyl ether, and the resulting insoluble material was filtered off. The filtrate was washed with 10% aqueous citric acid solution, a saturated aqueous sodium bicarbonate solution and brine subsequently, and dried over anhydrous magnesium sulfate. Removal of the solvent in vacuo gave ethyl N-[4-(2-hydroxyethyl)phenyl]aminoacetate (35.5 g).

Workup

  1. stirringthe resulting mixture was stirred for 1 hour
  2. filtrationThe insoluble material was filtered off
  3. concentrationthe filtrate was concentrated in vacuo
  4. additionTo the residue was added diethyl ether
  5. filtrationthe resulting insoluble material was filtered off
  6. washThe filtrate was washed with 10% aqueous citric acid solution
  7. dry with materiala saturated aqueous sodium bicarbonate solution and brine subsequently, and dried over anhydrous magnesium sulfate
  8. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-f1654327eae24a53b8d749af4a3065c5
Source dataset
uspto-grants-2002_03
Patent number
US06353025B1

Reaction notes

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