Piperidine → 1,3-Di-n-butyl-8-piperidino Xanthine

HRID 568139Notes

Reaction equation

HRID 568139 reaction equation
[CH2:1]([N:5]1[C:14](=[O:15])[C:13]2[NH:12][C:11](Br)=[N:10][C:9]=2[N:8]([CH2:17][CH2:18][CH2:19][CH3:20])[C:6]1=[O:7])[CH2:2][CH2:3][CH3:4].[NH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>C1(C)C=CC=CC=1>[CH2:1]([N:5]1[C:14](=[O:15])[C:13]2[NH:12][C:11]([N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)=[N:10][C:9]=2[N:8]([CH2:17][CH2:18][CH2:19][CH3:20])[C:6]1=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 101544891,3-Di-n-butyl-8-bromo Xanthine

Product 1

HCID 99243971,3-Di-n-butyl-8-piperidino Xanthine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1,3-Di-n-butyl-8-bromo xanthine (2 g, 0.0029 mol) was dissolved in toluene (50 ml). After addition of piperidine (5 g, 0.0058 mol) the mixture was refluxed for 9 hours. The reaction mixture was then extracted with water (4'30 ml), the organic layer dried over anhydrous sodium sulphate and the solvent removed in vacuo. The residue was recrystallised from ethanol to give the title product, yield 0.4 g (20%), m.pt. 221° C.

Workup

  1. temperaturewas refluxed for 9 hours
  2. extractionThe reaction mixture was then extracted with water (4'30 ml), the organic layer
  3. dry with materialdried over anhydrous sodium sulphate
  4. customthe solvent removed in vacuo
  5. customThe residue was recrystallised from ethanol

Sources & evidence

ORD record
ord-238baf31883a417f8d6abdd5f1ecee74
Source dataset
uspto-grants-2001_01
Patent number
US06180791B2

Reaction notes

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