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

HRID 3637Notes

Reaction equation

HRID 3637 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)
  3. dry with materialthe organic layer dried over anhydrous sodium sulphate
  4. customthe solvent removed in vacuo
  5. customThe residue was recrystallised from ethanol

Sources & evidence

ORD record
ord-fe8f501adbbe4ac2972456200d435247
Source dataset
uspto-grants-1998_03
Patent number
US05734051

Reaction notes

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