Ethanolamine → 2-((2-(Diethylamino)ethyl)amino)ethanol
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
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- temperatureAfter the reaction mixture was cooled to room temperature
- extractionthe mixture was extracted with chloroform (100 mL×6)
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- distillationThe resulting residue was distilled
Sources & evidence
- ORD record
- ord-43233ded123e49c5b26ca88fd5e20d8d
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07538224B2
Reaction notes
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