Morpholine → HCID 20672905, compound

HRID 1386501Notes

Reaction equation

HRID 1386501 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7](F)[CH:6]=[C:5]([O:10][CH3:11])[C:4]=1[C:12](=[O:16])[CH:13]([CH3:15])[CH3:14].[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[CH:6]=[C:5]([O:10][CH3:11])[C:4]=1[C:12](=[O:16])[CH:13]([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 21182091HCID 21182091, compound

Product 1

HCID 20672905HCID 20672905, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Into a 1-liter, three-necked round-bottom flask was placed 15.0 g (0.07 mole) of 1-(2,6-dimethoxy-4-fluorophenyl)-2-methylpropan-1-one produced in Example 12, 5.8 g (0.07 mole) of morpholine, and 19.0 g (0.14 mole) of K2CO3 in 100 ml. of dimethylsulfoxide (DMSO). The mixture was flushed with argon and heated to reflux overnight. The reaction mixture was cooled and then mixed with about 100 ml of distilled water and extracted with dichloromethane. The organic layer was washed with NaHCO3 solution, salt water, and then dried. The solvent was removed by vacuum to yield the final product, 1-(2,6-dimethoxy-4-morpholinophenyl)-2-methylpropan-1-one. The yield of the reaction was 18.1 g of product (88%).

Workup

  1. customThe mixture was flushed with argon
  2. temperatureheated
  3. temperatureto reflux overnight
  4. temperatureThe reaction mixture was cooled
  5. additionmixed with about 100 ml of distilled water
  6. extractionextracted with dichloromethane
  7. washThe organic layer was washed with NaHCO3 solution, salt water
  8. customdried
  9. customThe solvent was removed by vacuum

Sources & evidence

ORD record
ord-a5455fafa7c24e889ce872c2342a6247
Source dataset
uspto-grants-2001_07
Patent number
US06265458B1

Reaction notes

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