Methylhydrazine → 3-(1-acetyl-4-piperidinyl)-6-fluoro-1-methyl-1H-indazole

HRID 1722149Notes

Reaction equation

HRID 1722149 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10](=O)[C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=2F)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[CH3:20][NH:21][NH2:22]>C(O)CCC>[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[C:11]3[C:12](=[CH:13][C:14]([F:17])=[CH:15][CH:16]=3)[N:21]([CH3:20])[N:22]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 27407071-Acetyl-4-(2',4'-difluorobenzoyl)piperidine

Product 1

HCID 230482173-(1-acetyl-4-piperidinyl)-6-fluoro-1-methyl-1H-indazoleYield 108.7%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 5.0 g of 1-acetyl-4-(2,4-difluorobenzoyl)piperidine, 1.2 g of methylhydrazine and 50 ml of n-butanol was heated under reflux for 16 hrs. After cooling, the solvent was removed in vacuo and the residue was diluted with water. The aqueous mixture was made basic with ammonium hydroxide and extracted with dichloromethane. The organic extract was washed with water, dried over anhydrous magnesium sulfate and concentrated to yield 5.6 g of 3-(1-acetyl-4-piperidinyl)-6-fluoro-1-methyl-1H-indazole as an oil.

Workup

  1. temperatureunder reflux for 16 hrs
  2. temperatureAfter cooling
  3. customthe solvent was removed in vacuo
  4. additionthe residue was diluted with water
  5. extractionextracted with dichloromethane
  6. extractionThe organic extract
  7. washwas washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-01afaff7184e4d62901cf946ca9bcbda
Source dataset
uspto-grants-1989_08
Patent number
US04853470

Reaction notes

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