Potassium Carbonate → HCID 14552917, compound

HRID 2051175Notes

Reaction equation

HRID 2051175 reaction equation
Br[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=[O:4].[Cl: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.ClC1C=C2C(C(=O)CC(C3C=CC(C)=CC=3)=N2)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[Cl: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 67947242HCID 67947242, compoundHCID 67947403HCID 67947403, compound

Product 1

HCID 14552917HCID 14552917, compoundYield 13.6%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Conditions

Temperature
20 °C

Procedure

4-(2-Bromoacetyl)morpholine (7.9 g) in 2-butanone (50 cc) is added to a stirred suspension of a mixture (10 g) of 5-chloro-2-(4-methylphenyl)-4-quinolone and 7-chloro-2-(4-methylphenyl)-4-quinolone and anhydrous potassium carbonate (10.2 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 the residue has been chromatographed twice on silica gel, the first time using a chloroform/ethyl acetate mixture (70:30 by volume) and the second time using a chloroform/ethyl acetate mixture (80:20 by volume) as eluant, the solid obtained is recrystallized in ethyl acetate. 4-{[ 5-chloro-2-(4-methylphenyl)-4-quinolyl]oxyacetyl}morpholine (2 g), m.p. 170 ° 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 the residue has been chromatographed twice on silica gel
  10. customthe solid obtained
  11. customis recrystallized in ethyl acetate

Sources & evidence

ORD record
ord-407c59d8c6324013b7bbd51511ba3bd8
Source dataset
uspto-grants-1991_05
Patent number
US05017576

Reaction notes

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