2-(Dimethylamino)ethanol → N,N-dimethyl-2-(4-nitrophenoxy)ethanamine
Reaction equation
[H-].[Na+].[CH3:3][N:4]([CH3:8])[CH2:5][CH2:6][OH:7].F[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1>O1CCCC1>[CH3:3][N:4]([CH3:8])[CH2:5][CH2:6][O:7][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Sodium hydride (60% in oil, 1.04 g, 26 mmol) was placed in a round bottom flask and washed with hexanes and then was suspended in tetrahydrofuran and cooled to 0° C. A solution of 2-dimethylamino-ethanol (Aldrich, 1.78g, 20 mmol) in tetrahydrofuran was added and the suspension was stirred at 0° C. for 30 minutes and at room temperature for 1 hour. Then, the suspension was cooled to −20° C. and a solution of 4-fluoro nitrobenzene (Aldrich, 3.95g, 28 mmol) in tetrahydrofuran was added. The mixture was stirred for 2 hours by gradually increasing the temperature to around 5° C. The reaction was quenched by addition of 1N HCl and the mixture was washed with ether and basified with 1 N NaOH and extracted with diethyl ether. The extract was dried (Na2SO4) and concentrated to give a light yellow oil. 2.8 g, 66%. MS (ES) MH+=211.
Workup
- washwashed with hexanes
- temperatureThen, the suspension was cooled to −20° C.
- stirringThe mixture was stirred for 2 hours
- temperatureby gradually increasing the temperature to around 5° C
- customThe reaction was quenched by addition of 1N HCl
- washthe mixture was washed with ether and basified with 1 N NaOH
- extractionextracted with diethyl ether
- dry with materialThe extract was dried (Na2SO4)
- concentrationconcentrated
- customto give a light yellow oil
Sources & evidence
- ORD record
- ord-f7717dd2c90143348a290083793adedb
- Source dataset
- uspto-grants-2004_11
- Patent number
- US06818663B2
Reaction notes
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