Potassium Carbonate → N-Methyl-4-phenyl-4-piperidyl N-(8-trifluoromethyl-4-quinolyl)anthraniloyloxyacetate

HRID 1979728

Reaction equation

HRID 1979728 reaction equation
Cl.Cl[CH2:3][C:4]([O:6][C:7]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:12][CH2:11][N:10]([CH3:13])[CH2:9][CH2:8]1)=[O:5].[Na].[F:21][C:22]([F:44])([F:43])[C:23]1[CH:24]=[CH:25][CH:26]=[C:27]2[C:32]=1[N:31]=[CH:30][CH:29]=[C:28]2[NH:33][C:34]1[C:35](=[CH:39][CH:40]=[CH:41][CH:42]=1)[C:36]([OH:38])=[O:37].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:43][C:22]([F:21])([F:44])[C:23]1[CH:24]=[CH:25][CH:26]=[C:27]2[C:32]=1[N:31]=[CH:30][CH:29]=[C:28]2[NH:33][C:34]1[C:35](=[CH:39][CH:40]=[CH:41][CH:42]=1)[C:36]([O:38][CH2:3][C:4]([O:6][C:7]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:12][CH2:11][N:10]([CH3:13])[CH2:9][CH2:8]1)=[O:5])=[O:37]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 37541Floctafenic acidHCID 5360545SodiumHCID 20438865N-methyl-4-phenyl-4-piperidyl chloroacetate hydrochloride

Product 1

HCID 16206495N-Methyl-4-phenyl-4-piperidyl N-(8-trifluoromethyl-4-quinolyl)anthraniloyloxyacetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.52 g of N-methyl-4-phenyl-4-piperidyl chloroacetate hydrochloride, 1.77 g of the sodium salt of N-(8-trifluoromethyl-4-quinolyl)-anthranilic acid and 0.7 g of potassium carbonate in 10 ml of dimethylformamide was stirred for 48 hours at 20°-25° C. Upon completion of the reaction, the inorganic salts were filtered off. The solution was evaporated to dryness and treated with water, and the solid collected by filtration. This solid was then refluxed with hexane, filtered and recrystallized from hexane to provide the title compound. M.p. 144°-145° C., yield 1 g (35%).

Workup

  1. customUpon completion of the reaction
  2. filtrationthe inorganic salts were filtered off
  3. customThe solution was evaporated to dryness
  4. additiontreated with water
  5. filtrationthe solid collected by filtration
  6. temperatureThis solid was then refluxed with hexane
  7. filtrationfiltered
  8. customrecrystallized from hexane

Sources & evidence

ORD record
ord-d371c46e99a743ea9f658f34ff924290
Source dataset
uspto-grants-1984_11
Patent number
US04482561

Linked notes

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