Imidazole → 1-[3-(1-Imidazolyl)propyl]piperazine

HRID 1709282Notes

Reaction equation

HRID 1709282 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].C(OC([N:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH2:21]OS(C)(=O)=O)[CH2:15][CH2:14]1)=O)C.C(=O)([O-])O.[Na+]>C(OCC)(=O)C.CN(C)C=O>[N:1]1([CH2:21][CH2:20][CH2:19][N:16]2[CH2:17][CH2:18][NH:13][CH2:14][CH2:15]2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 147727951-Ethoxycarbonyl-4-(3-mesyloxypropyl)piperazine

Product 1

HCID 147727971-[3-(1-Imidazolyl)propyl]piperazineYield 71.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of imidazole 0.68 g and N,N-dimethylformamide 20 ml was added 60% sodium hydride 0.60 g under ice-cooling, followed by stirring at room temperature for 5 minutes. To the resultant mixture was added 1-ethoxycarbonyl-4-(3-mesyloxypropyl)piperazine 3.68 g and the mixture was stirred at room temperature overnight. To the reaction mixture were added saturated solution of sodium hydrogen carbonate 50 ml and ethyl acetate 200 ml and the organic layer was taken using a separating funnel, dried over anhydrous magnesium sulfate and the solvent distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography (eluent: 10% methanol-ethyl acetate), and dissolved in ethanol 25 ml. To the solution was added 10% sodium hydroxide 25 ml and the mixture refluxed overnight. After cooling, ethyl acetate 100 ml was added to the solution, the organic layer was separated, and the aqueous layer extracted with ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give 1.39 g of 1-[3-(1-imidazolyl)propyl]piperazine.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature overnight
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent distilled off under reduced pressure
  5. customThe resultant residue was purified by silica gel column chromatography (eluent: 10% methanol-ethyl acetate)
  6. dissolutiondissolved in ethanol 25 ml
  7. additionTo the solution was added 10% sodium hydroxide 25 ml
  8. temperaturethe mixture refluxed overnight
  9. temperatureAfter cooling
  10. additionethyl acetate 100 ml was added to the solution
  11. customthe organic layer was separated
  12. extractionthe aqueous layer extracted with ethyl acetate
  13. dry with materialdried over anhydrous sodium sulfate
  14. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b8792b125acf40f1bab91d65d28d089f
Source dataset
uspto-grants-1990_08
Patent number
US04948795

Reaction notes

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