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

HRID 652173Notes

Reaction equation

HRID 652173 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-e8cf67af43e8490a809d072dcb201c64
Source dataset
uspto-grants-1987_06
Patent number
US04670447

Reaction notes

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