Ethanolamine → 2-(4-Chloro-benzylamino)-ethanol

HRID 1532982Notes

Reaction equation

HRID 1532982 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].[OH-].[Na+].[Cl:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12]Cl)=[CH:10][CH:9]=1>C(O)(C)C>[Cl:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12][NH:4][CH2:3][CH2:1][OH:2])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 14798Sodium Hydroxide

Product 1

HCID 4244522-(4-Chloro-benzylamino)-ethanol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Ethanolamine (56.9 g, 931 mmol) and sodium hydroxide (7.44 g, 186 mmol) were mixed in isopropanol (50 ml) and 4-chlorobenzyl chloride (30 g, 186 mmol) was added at such a rate that a mild reflux was achieved. The mixture was then refluxed for another 30 min. Evaporation of the solvent was followed by the addition of methylene chloride (50 ml). The solids were filtered off and the solvent was evaporated from the filtrate. The residual oil was distilled under oil pump vacuum and the fraction at 125-126° C. (0.1 mm Hg) was collected. Yield 27 g, 78%.

Workup

  1. temperaturea mild reflux
  2. temperatureThe mixture was then refluxed for another 30 min
  3. customEvaporation of the solvent
  4. additionwas followed by the addition of methylene chloride (50 ml)
  5. filtrationThe solids were filtered off
  6. customthe solvent was evaporated from the filtrate
  7. distillationThe residual oil was distilled under oil pump vacuum
  8. customthe fraction at 125-126° C. (0.1 mm Hg) was collected

Sources & evidence

ORD record
ord-d2ab9dfb082246db8bf9048c5c9a5c53
Source dataset
uspto-grants-2001_03
Patent number
US06207662B1

Reaction notes

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