Sodium Hydroxide → 2-Amino-7-(p-chloro-benzyl)-6,7,8,9-tetrahydro-5H-pyrazino[2,3-d]azepine
Reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[CH2:11][CH2:10][N:9]([C:12](=O)[C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[CH2:8][CH2:7][C:6]=2[N:21]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1>[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[CH2:11][CH2:10][N:9]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[CH2:8][CH2:7][C:6]=2[N:21]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
3.7 gm (12.2 mmols) of 2-amino-7-(4-chloro-benzoyl)-6,7,8,9-tetrahydro-5H-pyrazino[2,3-d]-azepine were dissolved in 50 ml of absolute tetrahydrofuran, and the solution was added dropwise to a suspension of 2.8 gm (73.3 mmols) of lithium aluminum hydride in tetrahydrofuran. The mixture was stirred for 3 hours at room temperature, and then the excess lithium aluminum hydride was decomposed with 2N sodium hydroxide and the precipitated aluminate was filtered off. The filtrate was concentrated by evaporation and chromatographed on silicagel with ethyl acetate/methanol (5:1) as the mobile phase. Thereafter, the product was dissolved in absolute ether, and the solution was evaporated until crystallization commenced.
Workup
- filtrationthe precipitated aluminate was filtered off
- concentrationThe filtrate was concentrated by evaporation
- customchromatographed on silicagel with ethyl acetate/methanol (5:1) as the mobile phase
- dissolutionThereafter, the product was dissolved in absolute ether
- customthe solution was evaporated until crystallization
Sources & evidence
- ORD record
- ord-2cdbbcc2e537444eabd4f06b7affcad1
- Source dataset
- uspto-grants-1984_12
- Patent number
- US04486433
Reaction notes
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