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

HRID 1440111Notes

Reaction equation

HRID 1440111 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-c947c35cdfc54ccbb99f36d2941cb4b5
Source dataset
uspto-grants-1996_03
Patent number
US05496951

Reaction notes

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