Ethanolamine → 2-((2-(Diethylamino)ethyl)amino)ethanol

HRID 499894Notes

Reaction equation

HRID 499894 reaction equation
Cl.[CH2:2]([N:4]([CH2:8][CH3:9])[CH2:5][CH2:6]Cl)[CH3:3].[NH2:10][CH2:11][CH2:12][OH:13]>[OH-].[Na+]>[CH2:2]([N:4]([CH2:8][CH3:9])[CH2:5][CH2:6][NH:10][CH2:11][CH2:12][OH:13])[CH3:3]

Participants

4

Conditions

Temperature
120 °C

Procedure

A mixture of 2-(diethylamino)ethylchloride hydrochloride (18 g, 0.11 mol) and 2-aminoethanol (19 mL, 0.32 mol) was stirred at 120° C. for 5 hours. After the reaction mixture was cooled to room temperature, a 1.0 mol/L aqueous solution of sodium hydroxide (40 mL) was added thereto, and the mixture was extracted with chloroform (100 mL×6). The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting residue was distilled to obtain N,N-diethyl-N′-(2-hydroxyethyl)ethylenediamine (7.6 g, 45%).

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. extractionthe mixture was extracted with chloroform (100 mL×6)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. distillationThe resulting residue was distilled

Sources & evidence

ORD record
ord-96ce769876ce42f1b053223b60174588
Source dataset
uspto-grants-2010_08
Patent number
US07767693B2

Reaction notes

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