Hydrochloric Acid → 1H-Indazole, 6-fluoro-1-methyl-3-(4-piperidinyl)-, hydrochloride

HRID 867717Notes

Reaction equation

HRID 867717 reaction equation
C([N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[C:18]3[C:13](=[CH:14][C:15]([F:19])=[CH:16][CH:17]=3)[N:12]([CH3:20])[N:11]=2)[CH2:6][CH2:5]1)(=O)C.[ClH:21].[OH-].[Na+].C(OCC)(=O)C.Cl>C(OCC)(=O)C>[ClH:21].[F:19][C:15]1[CH:14]=[C:13]2[C:18]([C:10]([CH:7]3[CH2:8][CH2:9][NH:4][CH2:5][CH2:6]3)=[N:11][N:12]2[CH3:20])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21866389Hydrogen chloride-ethyl acetateHCID 230482173-(1-acetyl-4-piperidinyl)-6-fluoro-1-methyl-1H-indazole

Product 1

HCID 140326091H-Indazole, 6-fluoro-1-methyl-3-(4-piperidinyl)-, hydrochlorideYield 21%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 16.8 g of 3-(1-acetyl-4-piperidinyl)-6-fluoro-1-methyl-1H-indazole and 100 ml of 6N hydrochloric acid was heated under reflux for 4 hrs. The solution was cooled in an ice bath, 50% aqueous sodium hydroxide was added, dropwise, with stirring and the mixture was extracted with ethyl acetate. Concentration of the organic extract gave an oil. The oil was dissolved in ethyl acetate and a saturated solution of ethyl acetate-hydrogen chloride was added. The salt was recrystallized twice from trichloromethane-ether and then from isopropanol (charcoal) to yield 3.0 g (21%) of product, mp 256°-258° C.

Workup

  1. temperatureunder reflux for 4 hrs
  2. temperatureThe solution was cooled in an ice bath
  3. extractionthe mixture was extracted with ethyl acetate
  4. extractionConcentration of the organic extract
  5. customgave an oil
  6. customThe salt was recrystallized twice from trichloromethane-ether

Sources & evidence

ORD record
ord-d7be320e9f9e4cb1bf2a7857ecebe461
Source dataset
uspto-grants-1988_10
Patent number
US04775761

Reaction notes

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