Morpholine → HCID 23143871, compound

HRID 1985826Notes

Reaction equation

HRID 1985826 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH2:11][O:12][CH3:13].[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[Na+]>CS(C)=O.O>[CH3:13][O:12][CH2:11][O:10][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)[CH:6]=[O:7]

Participants

7

Reactant 4

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 23143885HCID 23143885, compound

Product 1

HCID 23143871HCID 23143871, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

4-Fluoro-3-methoxymethoxybenzaldehyde (1.12 g), morpholine (0.8 mL), potassium carbonate (1.26 g) and water (3 mL) were suspended in dimethylsulfoxide (10 mL), and the mixture was stirred at 100° C. for 18 hours. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=1/5) to give the title compound (0.8 g).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe obtained residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=1/5)

Sources & evidence

ORD record
ord-553720cc8b114b41ba1780ce6b421fa4
Source dataset
uspto-grants-2009_06
Patent number
US07547680B2

Reaction notes

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