Morpholine → 4-(Morpholinomethyl)phenyl acetate
Reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11]Cl)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1>O>[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To 4-(chloromethyl)phenyl acetate (2.5 g, 13.5 mmol) was added neat morpholine (3.0 mL, 34.4 mmol) at r.t. The solution was heated to 70° C. for 45 min, then cooled. Water (10 mL) was added and the solution was extracted with 10% methanol in dichloromethane (4×20 mL). The combined organics were washed with brine, dried with Na2SO4, and concentrated. Purification on silica gel (10% methanol/dichloromethane) gave the title compound.
Workup
- temperaturecooled
- extractionthe solution was extracted with 10% methanol in dichloromethane (4×20 mL)
- washThe combined organics were washed with brine
- dry with materialdried with Na2SO4
- concentrationconcentrated
- customPurification on silica gel (10% methanol/dichloromethane)
Sources & evidence
- ORD record
- ord-d273ad57696d4780bd06c83bb419e665
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08450348B2
Reaction notes
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