Water → HCID 178480240, compound

HRID 652158Notes

Reaction equation

HRID 652158 reaction equation
CO[C:3]([N:5]1[CH2:10][CH2:9][CH:8]([C:11]2[C:19]3[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=3)[NH:13][N:12]=2)[CH2:7][CH2:6]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[Cl:20][C:16]1[CH:15]=[C:14]2[C:19]([C:11]([CH:8]3[CH2:9][CH2:10][N:5]([CH3:3])[CH2:6][CH2:7]3)=[N:12][NH:13]2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 178501916HCID 178501916, compound

Product 1

HCID 178480240HCID 178480240, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution, under nitrogen, of 13.0 g of 4-(6-chloro-1H-indazol-3-yl)piperidine-1-carboxylic acid methyl ester in 150 ml of tetrahydrofuran was added, dropwise, 48 ml of a 1M solution of lithium aluminum hydride (0.048 mole) in tetrahydrofuran. The solution was stirred under reflux for 1 hr. The reaction mixture was cooled in an ice-salt bath and water was added slowly. The reaction mixture was filtered, the filter cake washed with tetrahydrofuran and methanol, and the filtrate was concentrated. Recrystallization of the residue from ethanol-water yielded 7.6 g (69%) of product, mp 211°-213° C.

Workup

  1. temperatureunder reflux for 1 hr
  2. temperatureThe reaction mixture was cooled in an ice-salt bath
  3. filtrationThe reaction mixture was filtered
  4. washthe filter cake washed with tetrahydrofuran and methanol
  5. concentrationthe filtrate was concentrated
  6. customRecrystallization of the residue from ethanol-water

Sources & evidence

ORD record
ord-d2bab2ef9b67470ab99277009e80e506
Source dataset
uspto-grants-1987_06
Patent number
US04670447

Reaction notes

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