Water → HCID 15485217, compound

HRID 1586463Notes

Reaction equation

HRID 1586463 reaction equation
[CH2:1]([N:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][NH:13][C:14]([C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]([CH2:25][CH2:26][CH3:27])[N:17]=2)=O)[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[CH2:1]([N:5]1[CH2:6][CH2:7][N:8]([CH2:11][CH2:12][NH:13][CH2:14][C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]([CH2:25][CH2:26][CH3:27])[N:17]=2)[CH2:9][CH2:10]1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 15435289HCID 15435289, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15485217HCID 15485217, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of N-[2-(4-n-butyl-1-piperazinyl)-ethyl]-1-n-propylindazole-3-carboxamide (0.36 g) obtained in Example 3 in THF (5 ml) was added lithium aluminum hydride (0.11 g) at room temperature, and the mixture was heated under reflux for 3 hours. The reaction solution was ice-cooled, and were successively added water (0.1 ml), a 15% aqueous sodium hydroxide (0.1 ml), water (0.3 ml) and THF (10 ml). After the reaction solution was stirred at room temperature for 30 minutes, the insolubles were filtered off with Celite. The filtrate was distilled off under reduced pressure, and the residue was purified by thin-layer chromatography on silica gel (chloroform:methanol:aqueous ammonia=8:2:0.2) to give the title compound (0.14 g) as a pale yellow oily substance. Yield=40%.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. temperaturecooled
  4. filtrationthe insolubles were filtered off with Celite
  5. distillationThe filtrate was distilled off under reduced pressure
  6. customthe residue was purified by thin-layer chromatography on silica gel (chloroform:methanol:aqueous ammonia=8:2:0.2)

Sources & evidence

ORD record
ord-d21c6a4967224611b0b83f84d66d2db1
Source dataset
uspto-grants-1999_08
Patent number
US05945434

Reaction notes

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