Ethanolamine → N,N-Dibenzylethanolamine

HRID 473603Notes

Reaction equation

HRID 473603 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].CO.O.[OH-].[Na+].[CH2:10](Cl)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH2:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.[C:24](OCC)(=O)C>>[CH2:10]([N:4]([CH2:24][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:3][CH2:1][OH:2])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 5

HCID 700EthanolamineHCID 7503Benzyl ChlorideHCID 14798Sodium HydroxideHCID 21867204Cyclohexane ethylacetateHCID 22242641Methanol--water (1/1)

Product 1

HCID 22657N,N-Dibenzylethanolamine

Procedure

To a vigorously stirred solution of 6.7 ml (1.12 mol, 1 equiv.) ethanolamine in 120 ml of (1/1) MeOH/H2O were added 7.2 g (1.8 mol, 1.6 equiv.) of sodium hydroxide and 24.6 g (1.8 mol., 1.6 eq). The suspension was refluxed for 30′ before addition of 24.5 ml (2.3 mol., 2 equiv.) of benzyl chloride. The mixture was refluxed overnight before cooled to room temperature and extracted with 3×160 ml of diethyl ether. The organic solution was dried over sodium sulphate, and evaporated. The residue was distilled Kugel Rohr (100° C., 1 mm Hg).

Workup

  1. temperatureThe suspension was refluxed for 30′
  2. temperatureThe mixture was refluxed overnight
  3. extractionextracted with 3×160 ml of diethyl ether
  4. dry with materialThe organic solution was dried over sodium sulphate
  5. customevaporated
  6. distillationThe residue was distilled Kugel Rohr (100° C., 1 mm Hg)

Sources & evidence

ORD record
ord-f53b23a75b40438d8c7aeb6e709d0aa4
Source dataset
uspto-grants-2014_01
Patent number
US08637496B2

Reaction notes

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