Dimethyl Sulfate → 8-(5-Hydroxypentylamino) caffeine

HRID 1721552Notes

Reaction equation

HRID 1721552 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]1[NH:17][C:16]2[C:15](=[O:18])[N:13]([CH3:14])[C:12](=[O:19])[N:11]([CH3:20])[C:10]=2[N:9]=1.[CH3:21]OS(OC)(=O)=O.[OH-].[Na+]>O>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]1[N:17]([CH3:21])[C:16]2[C:15](=[O:18])[N:13]([CH3:14])[C:12](=[O:19])[N:11]([CH3:20])[C:10]=2[N:9]=1

Participants

5

Reactant 3

HCID 6497Dimethyl Sulfate2×HCID 14798Sodium HydroxideHCID 224131858-(5-Hydroxypentylamino)theophylline2×

Product 1

HCID 571583678-(5-Hydroxypentylamino) caffeine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Beginning with 8-(5-hydroxypentylamino) theophylline in Example 3, 1.0 ml of dimethylsulfate (DMS) was added to 1.40 g of 8-(5-hydroxypentylamino) theophylline in 20 ml of water containing 0.3 g of sodiumhydroxide. The 1.0 ml DMS was added in 0.1 ml increments over of hour at: room temperature. A colorless crystalline solid separated and was collected by filtration. This solid was dried to provide 0.850 g of 8-(5-hydroxypentylamino) caffeine.

Workup

  1. customA colorless crystalline solid separated
  2. filtrationwas collected by filtration
  3. customThis solid was dried

Sources & evidence

ORD record
ord-0a2230f7c472450ebf275c1bd5fe3a1b
Source dataset
uspto-grants-1996_04
Patent number
US05512433

Reaction notes

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