Water → HCID 178462536, compound

HRID 1382574Notes

Reaction equation

HRID 1382574 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[C:18]3[C:13](=[CH:14][C:15]([F:19])=[CH:16][CH:17]=3)[NH:12][N:11]=2)[CH2:6][CH2:5]1)(=O)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH2:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[C:18]3[C:13](=[CH:14][C:15]([F:19])=[CH:16][CH:17]=3)[NH:12][N:11]=2)[CH2:6][CH2:5]1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 178473788HCID 178473788, compound

Product 1

HCID 178462536HCID 178462536, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension, under nitrogen, of 14.0 g of 3-(1-acetyl-4-piperidinyl)-6-fluoro-1H-indazole in 180 ml of tetrahydrofuran was added, dropwise, 55 ml of a 1M solution of lithium aluminum hydride in tetrahydrofuran. The reaction mixture was stirred under reflux for 1 hr and then stirred at ambient temperature for 15 hrs. The reaction mixture was cooled in an ice-salt bath and water was added slowly. The reaction mixture was filtered. The filter cake was washed with tetrahydrofuran and the filtrate was concentrated. Recrystallization of the residue from toluene afforded 9.0 g (68%) of product. Recrystallization of a 3.0 g sample from toluene yielded the analytical sample, mp 175°-178° C.

Workup

  1. temperatureunder reflux for 1 hr
  2. stirringstirred at ambient temperature for 15 hrs
  3. temperatureThe reaction mixture was cooled in an ice-salt bath
  4. filtrationThe reaction mixture was filtered
  5. washThe filter cake was washed with tetrahydrofuran
  6. concentrationthe filtrate was concentrated
  7. customRecrystallization of the residue from toluene

Sources & evidence

ORD record
ord-62df60eb600d401685c90f3742b83413
Source dataset
uspto-grants-1989_02
Patent number
US04806649

Reaction notes

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