4-Cyanophenol → 4-(2-Morpholin-4-ylethoxy)benzonitrile
Reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].[OH-].[Na+].Cl[CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1>CN(C=O)C>[N:15]1([CH2:14][CH2:13][O:9][C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 4-cyanophenol (5.95 g, 0.05 mol) in DMF (35 ml) at 0° C. is added 60% NaOH (2.2 g, 0.055 mol). The reaction mixture is stirred at 0° C. for 15 minutes, then at room temperature for 15 minutes and then N-(2-chloroethyl)morpholine (prepared from 11.16 g, 0.06 mol of the hydrochloride salt) is added, and the reaction mixture is stirred at room temperature for about two days. There is still a small amount of starting material present so the reaction mixture is heated on a steam bath for 4 hours. The reaction mixture is cooled to room temperature and then the solvent is removed. Ice water is added to the residue, and the solid which precipitats is collected by filtration and dried to afford 11.3 g (97%) of 4-[2-(4-morpholinyl)ethoxy]benzonitrile.
Workup
- waitat room temperature for 15 minutes
- additionis added
- stirringthe reaction mixture is stirred at room temperature for about two days
- temperatureis heated on a steam bath for 4 hours
- temperatureThe reaction mixture is cooled to room temperature
- customthe solvent is removed
- additionIce water is added to the residue
- customthe solid which precipitats
- filtrationis collected by filtration
- customdried
Sources & evidence
- ORD record
- ord-13955a05db6d47069211996762836819
- Source dataset
- uspto-grants-1998_12
- Patent number
- US05852035
Reaction notes
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