Theophylline → 7-[4-[4-(Trifluoromethyl)benzoyl]benzyl]-1,3-dimethylxanthine

HRID 1291302Notes

Reaction equation

HRID 1291302 reaction equation
[N:1]1([C:12](=[O:13])[C:11]2[NH:10][CH:9]=[N:8][C:7]=2[N:5]([CH3:6])[C:3]1=[O:4])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[F:20][C:21]([F:39])([F:38])[C:22]1[CH:37]=[CH:36][C:25]([C:26]([C:28]2[CH:35]=[CH:34][C:31]([CH2:32]Br)=[CH:30][CH:29]=2)=[O:27])=[CH:24][CH:23]=1>CN(C=O)C.O>[F:20][C:21]([F:38])([F:39])[C:22]1[CH:37]=[CH:36][C:25]([C:26]([C:28]2[CH:35]=[CH:34][C:31]([CH2:32][N:10]3[C:11]4[C:12](=[O:13])[N:1]([CH3:2])[C:3](=[O:4])[N:5]([CH3:6])[C:7]=4[N:8]=[CH:9]3)=[CH:30][CH:29]=2)=[O:27])=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 2153TheophyllineHCID 11430Potassium CarbonateHCID 189191184-(4-Trifluoromethylbenzoyl)benzyl bromide

Product 1

HCID 189190907-[4-[4-(Trifluoromethyl)benzoyl]benzyl]-1,3-dimethylxanthineYield 36%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of theophylline (1.80 g) in DMF (20 ml) were added potassium carbonate (1.66 g) and 4-[4-(trifluoromethyl)benzoyl]benzyl bromide (3.43 g) and the mixture was stirred at room temperature for 20 hours. This reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed with saturated aqueous NaCl solution and dried over anhydrous sodium sulfate and the solvent was distilled off. To the residue was added 4N-hydrogen chloride/ethyl acetate and the resulting precipitate was harvested by filtration. To this precipitate was added a saturated aqueous solution of NaHCO3 and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous NaCl solution and dried over anhydrous sodium sulfate and the solvent was distilled off to provide the title compound as colorless powder (1.57 g, 36%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated aqueous NaCl solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off
  5. additionTo the residue was added 4N-hydrogen chloride/ethyl acetate
  6. filtrationthe resulting precipitate was harvested by filtration
  7. additionTo this precipitate was added a saturated aqueous solution of NaHCO3
  8. extractionthe mixture was extracted with ethyl acetate
  9. washThe extract was washed with saturated aqueous NaCl solution
  10. dry with materialdried over anhydrous sodium sulfate
  11. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-dade393003cf41e7925cdafdfdde6680
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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