Ethanolamine → HCID 15192264, compound

HRID 749166Notes

Reaction equation

HRID 749166 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:12][CH:13]([O:16][CH3:17])[O:14][CH3:15]>O1CCOCC1>[NH3:4].[CH3:15][O:14][CH:13]([O:16][CH3:17])[CH2:12][NH:4][CH2:3][CH2:1][OH:2]

Participants

6

Reactant 3

HCID 700EthanolamineHCID 11430Potassium CarbonateHCID 816722-Bromo-1,1-dimethoxyethane

Product 2

HCID 222AmmoniaHCID 15192264HCID 15192264, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Ethanolamine (4 ml, 66.3 mmol) in dioxane (50 ml) in the presence of potassium carbonate (6.9 g, 50 mmol) was reacted with 2-bromo-1,1-dimethoxyethane (5 ml, 42.3 mmol) at 75° C. for 6 hours. The solid was filtered and washed with dioxane. The recovered organic phase was concentrated and purified by chromatography on silica gel. Elution with dichloromethane followed by increased polarity to dichloromethane:methanol (97:3), dichloromethane:methanolic ammonia (94:6) yielded 2-((2,2-dimethoxyethyl)amino)ethanol (2.4 g, 38% yield) as a pale yellow liquid:

Workup

  1. filtrationThe solid was filtered
  2. washwashed with dioxane
  3. concentrationThe recovered organic phase was concentrated
  4. custompurified by chromatography on silica gel
  5. washElution with dichloromethane
  6. temperatureby increased polarity to dichloromethane:methanol (97:3), dichloromethane

Sources & evidence

ORD record
ord-51ecec3f7fce4dac98f2049f448f1ae9
Source dataset
uspto-grants-2008_07
Patent number
US07402585B2

Reaction notes

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