Hydrochloric Acid → 3-(Piperazin-1-YL)-1H-indazole

HRID 742754Notes

Reaction equation

HRID 742754 reaction equation
C1(S([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([N:19]3[CH2:24][CH2:23][N:22](C(OC4C=CC=CC=4)=O)[CH2:21][CH2:20]3)=[N:11]2)(=O)=O)C=CC=CC=1.[OH-].[K+].Cl>C(O)C>[N:19]1([C:12]2[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[NH:10][N:11]=2)[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 184672231-Benzenesulfonyl-3-(1-phenoxycarbonyl4-piperazinyl)-1H-indazole

Product 1

HCID 148234453-(Piperazin-1-YL)-1H-indazoleYield 94.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 1-benzenesulfonyl-3-(1-phenoxycarbonyl-4-piperazinyl)-1H-indazole (31.3 g, 67.7 mmol) in ethanol (500 ml) was added 50% KOH (aq.) (100 g of KOH in 100 g H2O) at room temperature. The reaction mixture was warmed to reflux for 6.5 hours and cooled to room temperature. After adjusting the pH to about two using HCl (con., 120 ml), the volatiles were removed under reduced pressure. The remaining residue was diluted with water and removed via filtration. The aqueous filtrate was washed with EtOAc and basified to pH=8 using 50% NaOH (aq.). The product was extracted into 10:1 dichloromethane/isopropylalcohol. The combined organics were dried (MgSO4), filtered, and concentrated to give 13.0 g of desired 3-piperazin-1-yl-1H-indazole as a brown solid which was used without further purification.

Workup

  1. temperatureThe reaction mixture was warmed
  2. temperatureto reflux for 6.5 hours
  3. customthe volatiles were removed under reduced pressure
  4. additionThe remaining residue was diluted with water
  5. customremoved via filtration
  6. washThe aqueous filtrate was washed with EtOAc and basified to pH=8
  7. extractionThe product was extracted into 10:1 dichloromethane/isopropylalcohol
  8. dry with materialThe combined organics were dried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-4d9d306d346848da81159b7cf0dd25f6
Source dataset
uspto-grants-1996_09
Patent number
US05554614

Reaction notes

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