Enprofylline → 7-Benzyl-3-propylxanthine

HRID 323855

Reaction equation

HRID 323855 reaction equation
[OH-].[Na+].[CH2:3]([N:6]1[C:14]2[N:13]=[CH:12][NH:11][C:10]=2[C:9](=[O:15])[NH:8][C:7]1=[O:16])[CH2:4][CH3:5].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O.CO>[CH2:17]([N:11]1[C:10]2[C:9](=[O:15])[NH:8][C:7](=[O:16])[N:6]([CH2:3][CH2:4][CH3:5])[C:14]=2[N:13]=[CH:12]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 1676EnprofyllineHCID 7498Benzyl BromideHCID 14798Sodium Hydroxide

Product 1

HCID 220073027-Benzyl-3-propylxanthine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

4.12 g (0.103 mol) of sodium hydroxide dissolved in 41 ml of water were added to a suspension of 20 g (0.103 mol) of 3-propylxanthine in 112 ml of methanol and the reaction mixture was stirred at 70° C. for one hour, then treated dropwise at the same temperature with 12.23 ml (0.103 mol) of benzyl bromide and kept between 70° and 80° C. for 4 hours. The mixture was cooled, filtered cold on a suction filter, and the product was washed with water on the suction filter and dried under reduced pressure.

Workup

  1. waitkept between 70° and 80° C. for 4 hours
  2. temperatureThe mixture was cooled
  3. filtrationfiltered cold on a suction
  4. filtrationfilter
  5. washthe product was washed with water on the suction
  6. filtrationfilter
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-935c9152425340cfb9872e5686c8807b
Source dataset
uspto-grants-2001_04
Patent number
US06214992B1

Linked notes

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