Hydrazine hydrate (1:1) → 5-fluoro-3-(1-methyl-4-piperidinyl)-1H-indazole

HRID 845669Notes

Reaction equation

HRID 845669 reaction equation
F[C:2]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:3]=1[C:4]([CH:6]1[CH2:11][CH2:10][N:9]([CH3:12])[CH2:8][CH2:7]1)=O.O.[NH2:19][NH2:20]>O>[F:17][C:14]1[CH:13]=[C:3]2[C:2](=[CH:16][CH:15]=1)[NH:20][N:19]=[C:4]2[CH:6]1[CH2:11][CH2:10][N:9]([CH3:12])[CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 140324954-(2,5-Difluorobenzoyl)-1-methylpiperidine

Product 1

HCID 1784802385-fluoro-3-(1-methyl-4-piperidinyl)-1H-indazoleYield 22%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-(2,5-difluorobenzoyl)-1-methylpiperidine of Example 111 (38.5 g, 0.16 moles) and hydrazine monohydrate (79.5 g, 1.59 moles) was heated in an autoclave at 150° for 22 hours. The autoclave was cooled in an ice bath and then opened. The reaction mixture was poured into H2O, causing the product to crystallize. The product was collected and then recrystallized twice from toluene to yield 8.2 g (22%) of 5-fluoro-3-(1-methyl-4-piperidinyl)-1H-indazole, m.p. 202°-204°.

Workup

  1. temperaturewas heated in an autoclave at 150° for 22 hours
  2. temperatureThe autoclave was cooled in an ice bath
  3. customto crystallize
  4. customThe product was collected
  5. customrecrystallized twice from toluene

Sources & evidence

ORD record
ord-b688fc07c3934f0cb997543080fd2544
Source dataset
uspto-grants-1988_07
Patent number
US04758668

Reaction notes

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