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

HRID 2107424Notes

Reaction equation

HRID 2107424 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-a0340cf4f49347efb0c556af400ada4f
Source dataset
uspto-grants-1990_06
Patent number
US04933460

Reaction notes

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