Water → Azaquinzole

HRID 1045649Notes

Reaction equation

HRID 1045649 reaction equation
[CH2:1]1[CH:6]2[C:7]3[C:12]([CH2:13][CH2:14][N:5]2[C:4](=O)[CH2:3][NH:2]1)=[CH:11][CH:10]=[CH:9][CH:8]=3.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH2:1]1[CH:6]2[C:7]3[C:12]([CH2:13][CH2:14][N:5]2[CH2:4][CH2:3][NH:2]1)=[CH:11][CH:10]=[CH:9][CH:8]=3

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 6453168PraziquanamineHCID 21226445Aluminium lithium hydride

Product 1

HCID 179345AzaquinzoleYield 98.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,2,3,6,7,11b-Hexahydro-pyrazino[2,1-a]isoquinolin-4-one (3.03 g, 15.0 mmol) was added to a solution of lithium aluminum hydride (1.14 g, 30.0 mmol) in tetrahydrofuran (63 ml) and the mixture was refluxed for 6 hours. Water (1.2 ml), 15% aqueous sodium hydroxide (1.2 ml) and water (3.2 ml) were added sequentially to the ice-cooled solution, and filtration of the precipitate and removal of the solvent under reduced pressure afforded 1,3,4,6,7,11b-hexahydro-2H-pyrazino[2,1-a]isoquinoline (2.77 g, 98%).

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. temperaturecooled
  3. filtrationsolution, and filtration of the precipitate and removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-9c93d640c42347d59566728c667ee219
Source dataset
uspto-grants-2013_10
Patent number
US08569294B2

Reaction notes

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