Dimethylformamide → 12-formyl-2-methyl-3,4-dioxo-1,3,4,14b-tetrahydro-10H-pyrazino[1,2-a]pyrrolo[2,1-c][1,4]benzodiazepine
Reaction equation
P(Cl)(Cl)(Cl)=O.CN(C)[CH:8]=[O:9].[CH3:11][N:12]1[C:29](=[O:30])[C:28](=[O:31])[N:15]2[C:16]3[CH:27]=[CH:26][CH:25]=[CH:24][C:17]=3[CH2:18][N:19]3[CH:23]=[CH:22][CH:21]=[C:20]3[CH:14]2[CH2:13]1.C([O-])(=O)C.[Na+]>C(Cl)Cl.O>[CH:8]([C:23]1[N:19]2[C:20]([CH:14]3[CH2:13][N:12]([CH3:11])[C:29](=[O:30])[C:28](=[O:31])[N:15]3[C:16]3[CH:27]=[CH:26][CH:25]=[CH:24][C:17]=3[CH2:18]2)=[CH:21][CH:22]=1)=[O:9]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
The starting material is prepared as follows: The mixture of 170 mg of phosphorous oxychloride and 100 ml of dimethylformamide is stirred at room temperature for 30 minutes, whereupon the solution of 281 mg of 2-methyl-3,4-dioxo-1,3,4,14b-tetrahydro-10H-pyrazino[1,2-a]pyrrolo[2,1-c][1,4]benzodiazepine in 5 ml of methylene chloride is added dropwise. After 30 minutes, the mixture is refluxed for another 30 minutes and cooled to room temperature. It is combined with 1.5 g of sodium acetate in 5 ml of water, stirred for 30 minutes and the organic layer separated. It is washed with water, 5% aqueous sodium bicarbonate, dried, evaporated and the residue triturated with diethyl ether, to yield the 12-formyl-2-methyl-3,4-dioxo-1,3,4,14b-tetrahydro-10H-pyrazino[1,2-a]pyrrolo[2,1-c][1,4]benzodiazepine melting at 300°-302°.
Workup
- customThe starting material is prepared
- additionis added dropwise
- temperaturethe mixture is refluxed for another 30 minutes
- customthe organic layer separated
- washIt is washed with water, 5% aqueous sodium bicarbonate
- customdried
- customevaporated
- customthe residue triturated with diethyl ether
Sources & evidence
- ORD record
- ord-6dc6ee272bbc4d48aaba19afb4bf5492
- Source dataset
- uspto-grants-1982_12
- Patent number
- US04362666
Reaction notes
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