Piperazine → 5,11-dihydro-11-[3-(1-piperazinyl)-propionyl]-6H-pyrido-[2,3-b][1,4]-benzodiazepine-6-one
Reaction equation
Cl[CH2:2][CH2:3][C:4]([N:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[C:10](=[O:17])[NH:9][C:8]2[CH:18]=[CH:19][CH:20]=[N:21][C:7]1=2)=[O:5].[NH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>CC(N(C)C)=O.C(O)C>[N:22]1([CH2:2][CH2:3][C:4]([N:6]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[C:10](=[O:17])[NH:9][C:8]3[CH:18]=[CH:19][CH:20]=[N:21][C:7]2=3)=[O:5])[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A warm solution of 6.0 g of 11-(3-chloropropionyl)-5,11-dihydro-6H-pyrido-[2,3-b][1,4]-benzodiazepine-6-one in 12 ml of dimethylacetamide and 40 ml of ethanol was added dropwise with stirring to a refluxing solution of 8.6 g of piperazine in 50 ml of ethanol. Then, the reaction mixture was refluxed for 1 hour and the mixture was evaporated to dryness in vacuo. The residue was chromatographed over silica gel and the eluent was then evaporated to dryness in vacuo. The residue was crystallized from acetonitrile to obtain a 70% yield of 5,11-dihydro-11-[3-(1-piperazinyl)-propionyl]-6H-pyrido-[2,3-b][1,4]-benzodiazepine-6-one with a melting point of 280°-282° C. with decomposition.
Workup
- temperatureThen, the reaction mixture was refluxed for 1 hour
- customthe mixture was evaporated to dryness in vacuo
- customThe residue was chromatographed over silica gel
- customthe eluent was then evaporated to dryness in vacuo
- customThe residue was crystallized from acetonitrile
Sources & evidence
- ORD record
- ord-515cf680e6ca4dce968c58acaba8302c
- Source dataset
- uspto-grants-1980_07
- Patent number
- US04213985
Reaction notes
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