Sodium Hydroxide → HCID 14851751, compound

HRID 2165815Notes

Reaction equation

HRID 2165815 reaction equation
[CH3:1][N:2]1[C:10]2[N:9]=[CH:8][N:7]([CH2:11][CH2:12][CH3:13])[C:6]=2[C:5](=[O:14])[NH:4][C:3]1=[O:15].[Na].[CH3:17][O:18][C:19]1[CH:30]=[CH:29][C:22]([O:23][CH2:24][CH2:25][CH2:26][CH2:27]Br)=[CH:21][CH:20]=1.[OH-].[Na+]>C(O)C.O>[CH3:17][O:18][C:19]1[CH:30]=[CH:29][C:22]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][N:4]2[C:5](=[O:14])[C:6]3[N:7]([CH2:11][CH2:12][CH3:13])[CH:8]=[N:9][C:10]=3[N:2]([CH3:1])[C:3]2=[O:15])=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 20636681-(4-Bromobutoxy)-4-methoxybenzeneHCID 33143973-Methyl-7-propylpurine-2,6-dioneHCID 5360545Sodium

Product 1

HCID 14851751HCID 14851751, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

3-Methyl-7-propylxanthine (10.4 g) was dissolved in 200 ml of an ethanol/water (3:2 (v/v)) mixed solution containing 2.2 g of sodium hyddroxide and 15.5 g of 4-(4-methoxyphenoxy)butylbromide was added to the solution. The mixture was then refluxed at elevated temperatures for 12 hours. The reaction mixture was concentrated under reduced pressure to give the residual liquid which in turn was alkalized with 1N-sodium hydroxide solution and then extracted with chloroform. The extract was dried and concentrated under reduced pressure to dryness. The residue was then subjected to silica gel column chromatography using a chloroform/ethanol (40:1 (v/v)) eluent to yield 12.5 g (65%) of 1-[4-(4-methoxyphenoxy)butyl]-3-methyl-7-propylxanthine.

Workup

  1. additionmixed solution
  2. additionwas added to the solution
  3. temperatureThe mixture was then refluxed at elevated temperatures for 12 hours
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. customto give the residual liquid which in turn
  6. extractionextracted with chloroform
  7. customThe extract was dried
  8. concentrationconcentrated under reduced pressure to dryness

Sources & evidence

ORD record
ord-8a302079c7b040d2a37af0b7fb12e7b7
Source dataset
uspto-grants-1990_07
Patent number
US04942143

Reaction notes

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