Formaldehyde → 5-Fluoro-3-phenyl-1-(piperidin-1-ylmethyl)-1H-indazole

HRID 1730950Notes

Reaction equation

HRID 1730950 reaction equation
[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([F:16])[CH:14]=3)[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:17]=O.[NH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.[OH-].[Na+]>C(O)C>[N:19]1([CH2:17][N:9]2[C:10]3[C:15](=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[N:8]2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8082PiperidineHCID 14798Sodium HydroxideHCID 131437095-Fluoro-3-Phenyl-1H-Indazole

Product 1

HCID 214941985-Fluoro-3-phenyl-1-(piperidin-1-ylmethyl)-1H-indazoleYield 61.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Phenyl-5-fluoroindazole (2.12 g), paraformaldehyde (0.33 g), piperidine (1 g) and 1N aqueous sodium hydroxide solution (1 ml) were added to ethanol (30 ml) followed by heating under reflux for 3 hours. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in benzene, washed with water, dried over sodium sulfate and concentrated under reduced pressure to obtain 1.9 g of 1-piperidinomethyl-3-phenyl-5-fluoroindazole having a melting point between 82°-84° C after recrystallization from methanol.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 3 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in benzene
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a53ca93a68814163bd1a9cb457d535b6
Source dataset
uspto-grants-1976_11
Patent number
US03994890

Reaction notes

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