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

HRID 1382588Notes

Reaction equation

HRID 1382588 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-1dfa46b38661497d9eff776fb538e857
Source dataset
uspto-grants-1989_02
Patent number
US04806649

Reaction notes

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