Cesium carbonate → HCID 22496148, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[OH:12].Cl.Cl[CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[O:12][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
2-methoxy-5-nitrophenol (254 mg, 1.5 mmol, 1 eq.) was placed in dimethylformamide (3 mL) with 4-(2-chloro-ethyl)morpholine hydrochloride (837 mg, 4.5 mmol, 3 eq.), Cs2CO3 (3.4 g, 10.7 mmol, 7 eq.), KI (547 mg, 3.3 mmol, 2.2 eq.). The reaction mixture was heated at 80° C. and stirred for 20 hours. The reaction mixture was then concentrated under reduced pressure and the resulting residue was diluted with ethyl acetate. The organic phase was washed with a 1% NaOH aqueous solution, dried over MgSO4, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel to afford 4-(2-(2-methoxy-5-nitrophenoxy)ethyl)morpholine (386 mg, 91%).
Workup
- concentrationThe reaction mixture was then concentrated under reduced pressure
- additionthe resulting residue was diluted with ethyl acetate
- washThe organic phase was washed with a 1% NaOH aqueous solution
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe resulting residue was purified by column chromatography on silica gel
Sources & evidence
- ORD record
- ord-b054c81b4ad547029a81665eb5b82ad7
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09061999B2
Reaction notes
Loading…