Bromotheophylline → 8-(5-Hydroxypentylamino)theophylline

HRID 1721551Notes

Reaction equation

HRID 1721551 reaction equation
Br[C:2]1[NH:11][C:10]2[C:9](=[O:12])[N:7]([CH3:8])[C:6](=[O:13])[N:5]([CH3:14])[C:4]=2[N:3]=1.[NH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21]>CC1C=CC(C)=CC=1>[OH:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][NH:15][C:2]1[NH:11][C:10]2[C:9](=[O:12])[N:7]([CH3:8])[C:6](=[O:13])[N:5]([CH3:14])[C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 11808BromotheophyllineHCID 756345-Aminopentan-1-ol

Product 1

HCID 224131858-(5-Hydroxypentylamino)theophyllineYield 66.6%

Reagents, catalysts & solvents 1

HCID 7809P-XyleneSolvent

Procedure

A solution of 5.16 grams of 8-bromotheophylline and 5.15 grams of 5-amino-1 pentanol in 18 ml of p-xylene was refluxed for 18 hours. The reaction solution was allowed to cool and upon cooling to room temperature formed a solid/liquid mixture. The xylene was decanted and the solid was washed with pentane (3×40 ml). The resulting solid was stirred in 20 ml of water for 30 minutes and filtered to collect the solid material. The collected solid material was washed with water (3×20 ml), and dried to provide 3.73 g of 8-(5-hydroxypentylamino)theophylline. To a solution of 1.12 g of 8-(5-hydroxypentylamino)theophylline in 15 ml of anhydrous N,N-dimethylformamide (DMF) was added 0.516 g of succinic anhydride and 0.2 g of 4-dimethylamino pyridine (DMAP). The mixture was stirred with a magnetic stirrer overnight at room temperature under anhydrous conditions. The colorless solid that precipitated was collected by vacuum filtration, washed with dichloromethane and air dried to provide 1.20 g of theophylline-8-N-(5-hydroxypentylamino)-O-succinic acid ester. This solid was recrystallized from a boiling 1:1 propanol/water mixture and dried over calcium sulfate to provide a colorless solid.

Workup

  1. temperatureto cool
  2. customformed a solid/liquid mixture
  3. customThe xylene was decanted
  4. washthe solid was washed with pentane (3×40 ml)
  5. filtrationfiltered
  6. customto collect the solid material
  7. washThe collected solid material was washed with water (3×20 ml)
  8. customdried

Sources & evidence

ORD record
ord-e6f5815df17e435c932248ba542e782f
Source dataset
uspto-grants-1996_04
Patent number
US05512433

Reaction notes

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