Sodium Hydroxide → 2-Amino-7-(p-chloro-benzoyl)-6,7,8,9-tetrahydro-5H-pyrazino[2,3-d]azepine
Reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([N:8]2[CH2:14][CH2:13][C:12](=O)[C:11](=O)[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.ClC1C=CC(C(N2CCCC(=O)C(=O)C2)=O)=CC=1.Br.Br.[NH2:39][CH2:40][C:41]([NH2:43])=[NH:42].[OH-].[Na+]>CO.C(OCC)(=O)C>[NH2:43][C:41]1[CH:40]=[N:39][C:12]2[CH2:13][CH2:14][N:8]([C:6](=[O:7])[C:5]3[CH:17]=[CH:18][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH2:9][CH2:10][C:11]=2[N:42]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
53 mg (0.2 mol) of a mixture of 1-(4-chloro-benzoyl)-hexahydroazepine-4,5-dione and 1-(4-chloro-benzoyl)-hexahydroazepine-3,4-dione [prepared from 1-(4-chloro-benzoyl)-hexahydroazepine-4-one by selenium dioxide oxidation in dioxane/water] and 47 gm (0.2 mol) of 2-amino-acetamidine dihydrobromide were dissolved in 700 ml of methanol, and 200 ml of 2 N sodium hydroxide were added dropwise to the solution at 5° C. The mixture was stirred at room temperature for one hour, then concentrated by evaporation and then, after addition of more sodium hydroxide, extracted with chloroform. The dried extract solution was concentrated by evaporation and chromatographed on silicagel with ethyl acetate/methanol (10:1) as the mobile phase. The crystals obtained thereby were digested with ethyl acetate and suction-filtered.
Workup
- concentrationconcentrated by evaporation
- additionafter addition of more sodium hydroxide
- extractionextracted with chloroform
- extractionThe dried extract solution
- concentrationwas concentrated by evaporation
- customchromatographed on silicagel with ethyl acetate/methanol (10:1) as the mobile phase
- customThe crystals obtained
- filtrationsuction-filtered
Sources & evidence
- ORD record
- ord-471e56e0d4474346be64018e123719f9
- Source dataset
- uspto-grants-1983_10
- Patent number
- US04409220
Reaction notes
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