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 2 N 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-abdb304e32df4506930196dcc78f6574
- Source dataset
- uspto-grants-1983_10
- Patent number
- US04409220
Reaction notes
Loading…