Benzylethanolamine → N-benzyl-N-(3-fluoro-2-hydroxypropyl)ethanolamine

HRID 1461041Notes

Reaction equation

HRID 1461041 reaction equation
[CH2:1]([CH:3]1[O:5][CH2:4]1)[F:2].[CH2:6]([NH:13][CH2:14][CH2:15][OH:16])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(O)C>[CH2:6]([N:13]([CH2:4][CH:3]([OH:5])[CH2:1][F:2])[CH2:14][CH2:15][OH:16])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 4348BenzylethanolamineHCID 104181,2-Epoxy-3-fluoropropane

Product 1

HCID 18985353N-benzyl-N-(3-fluoro-2-hydroxypropyl)ethanolamineYield 95.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 22.20 g (0.3 mole) of epifluorohydrin and 67.95 g (0.45 mole) of N-benzylethanolamine dissolved in 200 ml of ethanol was heated under reflux for 5 hours. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure, and the residue was purified by column chromatography through silica gel using ethyl acetate as the eluent, to give 64.93 g of N-benzyl-N-(3-fluoro-2-hydroxypropyl)ethanolamine as a colorless oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
  4. customthe residue was purified by column chromatography through silica gel

Sources & evidence

ORD record
ord-e864a0dc3dfd406ab6a8e1170b3eaf58
Source dataset
uspto-grants-1991_12
Patent number
US05073556

Reaction notes

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