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

HRID 266014Notes

Reaction equation

HRID 266014 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>CCO>[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-aminoethoxy) ethanol and 144.6 g (1.046 mol) of potassium carbonate in 600 ml of EtOH/60 ml of water is heated to 60° C. To this mixture is added dropwise within one hour 178.95 g (1.046 mol) of benzyl bromide and then the mixture is refluxed for 2 hours, evaporated under vacuum, the residue taken up with 1 liter of methylene chloride, and filtered off from the salts. The filtrate is concentrated under vacuum and purified by flash chromatography (silica gel/mobile phase: methylene chloride/hexane/acetone:10/5/1). Yield: 127.58 g (94% of theory) of a colorless oil.

Workup

  1. temperaturethe mixture is refluxed for 2 hours
  2. customevaporated under vacuum
  3. filtrationfiltered off from the salts
  4. concentrationThe filtrate is concentrated under vacuum
  5. custompurified by flash chromatography (silica gel/mobile phase: methylene chloride/hexane/acetone:10/5/1)

Sources & evidence

ORD record
ord-4fd9977714574a539a47558061a28866
Source dataset
uspto-grants-1997_07
Patent number
US05650136

Reaction notes

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