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

HRID 1291303Notes

Reaction equation

HRID 1291303 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+].[N:20]1([C:29]([C:31]2[CH:38]=[CH:37][C:34]([CH2:35]Cl)=[CH:33][CH:32]=2)=[O:30])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21]1>CN(C=O)C.O>[N:20]1([C:29]([C:31]2[CH:32]=[CH:33][C:34]([CH2:35][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:37][CH:38]=2)=[O:30])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21]1

Participants

6

Reactant 3

HCID 2153TheophyllineHCID 11430Potassium CarbonateHCID 189191004-[(1-Indolyl)carbonyl]benzyl chloride

Product 1

HCID 189188807-[4-(1-Indolylcarbonyl)benzyl]-1,3-dimethylxanthineYield 54.5%

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-[(1-indolyl)carbonyl]benzyl chloride (2.70 g) and the mixture was stirred at room temperature for 22 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 provide the title compound as colorless powder (2.25 g, 54%).

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

Sources & evidence

ORD record
ord-b86156f0de2e4d929616b4fead64b1b5
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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