Theophylline → HCID 20244075, compound

HRID 462420Notes

Reaction equation

HRID 462420 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].[OH-].[Na+].Cl[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][OH:24]>O.CO>[CH3:2][N:1]1[C:12](=[O:13])[C:11]2[N:10]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][OH:24])[CH:9]=[N:8][C:7]=2[N:5]([CH3:6])[C:3]1=[O:4]

Participants

6

Reactant 3

HCID 2153TheophyllineHCID 14798Sodium HydroxideHCID 919521-Heptanol, 7-chloro-

Product 1

HCID 20244075HCID 20244075, compoundYield 21.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

18 g of theophylline are added under stirring at room temperature to a solution of 4.1 g of sodium hydroxide in 50 ml of water and 50 ml of methanol. After stirring the mixture at 70° C. 15.8 g of 7-chloro-1-heptanol are added. The mixture is then maintained at 70° C. for 22 hours and then it is subjected to evaporation under reduced pressure until it is dry. The residue is dissolved in 150 ml of 1-N-sodium hydroxide and the mixture is extracted with methylene chloride. After washing out with water and drying over sodium sulfate the methylene chloride solution is concentrated under reduced pressure and the oily residue is several times recrystallized from diisopropyl ether. 6.3 g of 1,3-dimethyl-7-(7'-hydroxyheptyl)-xanthine are obtained (yield, referred to reacted theophylline, =79.3%).

Workup

  1. temperatureThe mixture is then maintained at 70° C. for 22 hours
  2. customit is subjected to evaporation under reduced pressure until it
  3. customis dry
  4. dissolutionThe residue is dissolved in 150 ml of 1-N-sodium hydroxide
  5. extractionthe mixture is extracted with methylene chloride
  6. washAfter washing out with water
  7. dry with materialdrying over sodium sulfate the methylene chloride solution
  8. concentrationis concentrated under reduced pressure
  9. customrecrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-bbc078769bf04803a6b0cdc73bbf1f9a
Source dataset
uspto-grants-1985_05
Patent number
US04515795

Reaction notes

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