Water → HCID 21995804, compound
Reaction equation
[CH2:1]([N:3]([CH2:10][CH2:11][OH:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].[H-].[Na+].[CH2:15](I)[CH2:16][CH3:17].O>CN(C=O)C>[CH2:1]([N:3]([CH2:10][CH2:11][O:12][CH2:15][CH2:16][CH3:17])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH3:2]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 2-(N-ethylanilino)ethanol (17.83 g) in DMF (300 ml) was added at 0° C. sodium hydride (60%, 4.74 g), and the mixture was stirred at 0° C. for 30 minutes and at room temperature for 30 minutes. To the mixture was added propyl iodide (11.0 ml), and the mixture was stirred at 50° C. for 19 hours. To the mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure, and the residue was purified with silica gel column chromatography (ethyl acetate/hexane=1:19) to give colorless oil of N-ethyl-N-(2-propoxyethyl)aniline (10.18 g).
Workup
- stirringthe mixture was stirred at 50° C. for 19 hours
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with water and saturated brine
- dry with materialdried with magnesium sulfate
- concentrationconcentrated under reduced pressure
- customthe residue was purified with silica gel column chromatography (ethyl acetate/hexane=1:19)
Sources & evidence
- ORD record
- ord-aa4cdd2dd0274afba60011b54ee509ba
- Source dataset
- uspto-grants-2001_05
- Patent number
- US06235771B1
Reaction notes
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