Ethyl Acetate → Benzyl piperazine-1-carboxylate

HRID 863813Notes

Reaction equation

HRID 863813 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.[OH-].[Na+].C(OCC)(=O)C>Cl.O1CCOCC1>[CH2:17]([O:16][C:14]([N:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)=[O:15])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 15016698Benzyl tert-butyl piperazine-1,4-dicarboxylate

Product 1

HCID 643495Benzyl piperazine-1-carboxylateYield 159.6%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

N-tert-butyloxycarbonyl--N'-benzyloxycarbonyl-piperazine (1.8 g, 3.13 mmol) was dissolved in 10 mL of 4N-HCl/dioxane. It was stirred at room temperature for 30 minutes. The reaction mixture was cooled in an ice bath, 1N-NaOH solution was carefully added to the mixture to adjust pH above 10. Ethyl acetate (50 mL×3) was used to extract the compound. The combined ethyl acetate layers were washed with brine, dried over anhydrous sodium sulfate. After removal of the solvent, 1.1 g of N-benzyloxycarbonyl-piperazine was obtained in quantitative yield.

Workup

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. extractionto extract the compound
  3. washThe combined ethyl acetate layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter removal of the solvent

Sources & evidence

ORD record
ord-f538866a62a94b3f87cb505e7e282844
Source dataset
uspto-grants-1996_10
Patent number
US05561140

Reaction notes

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