Water → 2-(2-(Dibenzylamino)ethoxy)ethanol

HRID 1417119Notes

Reaction equation

HRID 1417119 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][OH:7].C(=O)([O-])[O-].[K+].[K+].O.[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(O)C>[CH2:15]([N:1]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:2][CH2:3][O:4][CH2:5][CH2:6][OH:7])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 13578Diglycolamine

Product 1

HCID 158924642-(2-(Dibenzylamino)ethoxy)ethanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 50 g (475.56 mmol) of 2-(2-amino-ethoxy)-ethanol and 144.6 g (1.046 mol) of potassium carbonate in 600 ml of ethanol/60 ml of water is heated to 60° C. 178.95 g (1.046 mol) of benzyl bromide is instilled in this mixture within 1 hour and then refluxed for 2 hours. It is concentrated by evaporation in a vacuum, the residue is taken up with 1 l of dichloromethane and filtered off from the salts. The filtrate is concentrated by evaporation in a vacuum and purified by flash chromatography on silica gel. (Mobile solvent: dichloromethane/hexane/acetone: 10/5/1)

Workup

  1. temperaturerefluxed for 2 hours
  2. concentrationIt is concentrated by evaporation in a vacuum
  3. filtrationfiltered off from the salts
  4. concentrationThe filtrate is concentrated by evaporation in a vacuum
  5. custompurified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-63d5fbb4655e4452ac95ccb8726af1b9
Source dataset
uspto-grants-1999_03
Patent number
US05876698

Reaction notes

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