Water → 6-(3-Aminopropoxy)carbostyril

HRID 1856750Notes

Reaction equation

HRID 1856750 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]([CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[NH:20][C:19](=[O:24])[CH:18]=[CH:17]2)=[N+]=[N-].O.[OH-].[Na+]>O1CCCC1>[NH2:7][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[NH:20][C:19](=[O:24])[CH:18]=[CH:17]2

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 221326056-(3-Azidopropoxy)carbostyril

Product 1

HCID 100136326-(3-Aminopropoxy)carbostyrilYield 69.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (1.9 g) in anhydrous tetrahydrofuran (50 ml) is added dropwise with stirring a solution of 6-(3-azidopropoxy)carbostyril (10 g) in anhydrous tetrahydrofuran (200 ml) under ice-cooling. The mixture is stirred at room temperature for one hour, and thereto are added dropwise water (2 ml), a 15% aqueous sodium hydroxide solution (2 ml) and water (6 ml). The insoluble materials are collected by filtration, and added to a mixture of chloroform-methanol (8: 1). The mixture is heated, and then cooled. The insoluble material are removed by filtration. The filtrate is concentrated under reduced pressure to remove the solvent, and thereto is added diethyl ether. The precipitated crystals are collected by filtration to give 6-(3-aminopropoxy)carbostyril (6.2 g) as a white powder.

Workup

  1. additionis added dropwise
  2. temperaturecooling
  3. filtrationThe insoluble materials are collected by filtration
  4. additionadded to a mixture of chloroform-methanol (8: 1)
  5. temperatureThe mixture is heated
  6. temperaturecooled
  7. customThe insoluble material are removed by filtration
  8. concentrationThe filtrate is concentrated under reduced pressure
  9. customto remove the solvent
  10. additionis added diethyl ether
  11. filtrationThe precipitated crystals are collected by filtration

Sources & evidence

ORD record
ord-2639c4105cda42db99d075ec0b8360cc
Source dataset
uspto-grants-2000_11
Patent number
US06143763

Reaction notes

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