Water → HCID 178480240, compound

HRID 986136Notes

Reaction equation

HRID 986136 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-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-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-e1cd4228af8646ef8c26bcd94b5afd70
Source dataset
uspto-grants-1987_12
Patent number
US04710573

Reaction notes

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