Potassium Carbonate → HCID 131716893, compound

HRID 2051177Notes

Reaction equation

HRID 2051177 reaction equation
Br[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=[O:4].[F:11][C:12]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:13]=1[C:14](=[O:29])[CH2:15][C:16]([C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=1)=[N:17]2.FC1C=C2C(C(=O)CC(C3C=CC(C)=CC=3)=N2)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[F:11][C:12]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:13]=1[C:14]([O:29][CH2:2][C:3]([N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=[O:4])=[CH:15][C:16]([C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=1)=[N:17]2

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 139968762-Bromo-1-(morpholin-4-yl)ethan-1-oneHCID 67947591HCID 67947591, compoundHCID 67947630HCID 67947630, compound

Product 1

HCID 131716893HCID 131716893, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Conditions

Temperature
20 °C

Procedure

4-(2-Bromoacetyl)morpholine (7.3 g) in 2 butanone (50 cc) is added to a stirred suspension of a mixture (11.2 g of 5-fluoro-2-(4-methylphenyl)-4-quinolone and 7-fluoro-2-(4-methylphenyl)-4-quinolone and anhydrous potassium carbonate (11.3 g) in 2-butanone (250 cc). The mixture is heated to reflux for 15 hours and cooled to room temperature (approximately 20° C.), the insoluble matter is removed by filtration and the 2-butanone is evaporated off under reduced pressure. The residue is taken up with water (200 cc) and the aqueous phase is extracted with methylene chloride (3×100 cc). The organic phase is separated after settling has taken place, dried and evaporated under reduced pressure. After chromatography of the residue on silica gel by means of cyclohexane/ethyl acetate mixture (70:30 by volume) as eluant, the solid obtained is ground in 40°-60° C. petroleum ether (100 cc). 4-≡[5-fluoro-2-(4-methylphenyl-4-quinolyl]oxyacetyl}morpholine (2.4 g), m.p. 142°-4° C., is thereby obtained.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 15 hours
  3. customthe insoluble matter is removed by filtration
  4. customthe 2-butanone is evaporated off under reduced pressure
  5. extractionthe aqueous phase is extracted with methylene chloride (3×100 cc)
  6. customThe organic phase is separated after settling
  7. customdried
  8. customevaporated under reduced pressure
  9. customAfter chromatography of the residue on silica gel by means of cyclohexane/ethyl acetate mixture (70:30 by volume) as eluant, the solid obtained
  10. customis ground in 40°-60° C.

Sources & evidence

ORD record
ord-3f6e8878ee6c4ff297841baabf305469
Source dataset
uspto-grants-1991_05
Patent number
US05017576

Reaction notes

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