Ethanolamine → HCID 60684367, compound

HRID 749169Notes

Reaction equation

HRID 749169 reaction equation
Br[CH2:2][CH2:3][C:4]([F:7])([F:6])[F:5].C(=O)([O-])[O-].[K+].[K+].[CH2:14]([CH2:16][NH2:17])[OH:15]>O1CCOCC1>[NH3:17].[F:5][C:4]([F:7])([F:6])[CH2:3][CH2:2][NH:17][CH2:16][CH2:14][OH:15]

Participants

6

Reactant 3

HCID 700EthanolamineHCID 11430Potassium CarbonateHCID 27251143-Bromo-1,1,1-trifluoropropane

Product 2

HCID 222AmmoniaHCID 60684367HCID 60684367, compoundYield 111.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-bromo-1,1,1-trifluoropropane (5.5 ml, 51.65 mmol) in dioxane (50 ml) in the presence of potassium carbonate (14.15 g, 102.5 mmol) was reacted with ethanolamine (3.0 ml, 51 mmol) at 60° C. for 36 hours. The solvent was evaporated and the residue purified by chromatography on silica gel. Elution with dichloromethane:methanol (95:5) then increased polarity to dichloromethane:methanolic ammonia (95:5) yielded 2-((3,3,3-trifluoropropyl)amino)ethanol (4.47 g, 55% yield):

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified by chromatography on silica gel
  3. washElution with dichloromethane:methanol (95:5)
  4. temperaturethen increased polarity to dichloromethane

Sources & evidence

ORD record
ord-b2da1998d9944288911a2e3231352c56
Source dataset
uspto-grants-2008_07
Patent number
US07402585B2

Reaction notes

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