Water → 4-tert-Butoxycarbonyl-1-[(3-hydroxy-1-propyl)sulfonyl]piperazine

HRID 352765Notes

Reaction equation

HRID 352765 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:14]([CH2:17][CH2:18][CH2:19]Cl)(=[O:16])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])(=[O:23])C.[K+].O.C(=O)(O)[O-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:14]([CH2:17][CH2:18][CH2:19][OH:23])(=[O:16])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 517044Potassium AcetateHCID 227098904-tert-Butoxycarbonyl-1-[(3-chloro-1-propyl)sulfonyl]piperazine

Product 1

HCID 227098864-tert-Butoxycarbonyl-1-[(3-hydroxy-1-propyl)sulfonyl]piperazine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

In N,N-dimethylformamide (10 ml), 4-tert-butoxycarbonyl-1-[(3-chloro-1-propyl)sulfonyl]piperazine (1.18 g) was dissolved, followed by the addition of potassium acetate (1.06 g). After stirring at room temperature for 2 hours, the reaction mixture was stirred under heat at 100° C. for 3 hours. The reaction mixture was diluted with ethyl acetate, followed by the addition of water and a saturated aqueous solution of sodium bicarbonate. After stirring, the organic layer so separated was washed with a 5% aqueous citric acid solution, water and saturated aqueous NaCl solution. After drying over anhydrous sodium sulfate, the residue obtained by distilling off the solvent under reduced pressure was dissolved in tetrahydrofuran (20 ml). To the resulting solution, water and lithium hydroxide monohydrate (221 mg) were added, followed by stirring at room temperature for 18 hours. Ethyl acetate and saturated aqueous NaCl solution were added to the reaction mixture to separate an organic layer. From the water layer, another organic layer was extracted with ethyl acetate. The organic layers were combined together, washed with saturated aqueous NaCl solution and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure. The residue was recrystallized from a mixed solvent of ethyl acetate an hexane, whereby the title compound (944 mg, 84%) was obtained.

Workup

  1. stirringthe reaction mixture was stirred
  2. temperatureunder heat at 100° C. for 3 hours
  3. stirringAfter stirring
  4. customthe organic layer so separated
  5. washwas washed with a 5% aqueous citric acid solution, water and saturated aqueous NaCl solution
  6. dry with materialAfter drying over anhydrous sodium sulfate
  7. customthe residue obtained
  8. distillationby distilling off the solvent under reduced pressure
  9. dissolutionwas dissolved in tetrahydrofuran (20 ml)
  10. additionTo the resulting solution, water and lithium hydroxide monohydrate (221 mg) were added
  11. stirringby stirring at room temperature for 18 hours
  12. additionEthyl acetate and saturated aqueous NaCl solution were added to the reaction mixture
  13. customto separate an organic layer
  14. extractionFrom the water layer, another organic layer was extracted with ethyl acetate
  15. washwashed with saturated aqueous NaCl solution
  16. dry with materialdried over anhydrous sodium sulfate
  17. distillationThe solvent was then distilled off under reduced pressure
  18. customThe residue was recrystallized from a mixed solvent of ethyl acetate an hexane, whereby the title compound (944 mg, 84%)
  19. customwas obtained

Sources & evidence

ORD record
ord-4a82659eab2146eaaa971f348b2f7eb0
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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