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

HRID 1902199Notes

Reaction equation

HRID 1902199 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

7

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 517045Sodium AcetateHCID 128377152-methyl-3,4-dioxo-1,2,4,14b-tetrahydro-10H-pyrazino[1,2-a]pyrrolo[2,1-c][1,4]benzodiazepine

Product 1

HCID 1283778412-formyl-2-methyl-3,4-dioxo-1,3,4,14b-tetrahydro-10H-pyrazino[1,2-a]pyrrolo[2,1-c][1,4]benzodiazepine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

The mixture of 170 mg of phosphorus 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

  1. additionis added dropwise
  2. temperaturethe mixture is refluxed for another 30 minutes
  3. customthe organic layer separated
  4. washIt is washed with water, 5% aqueous sodium bicarbonate
  5. customdried
  6. customevaporated
  7. customthe residue triturated with diethyl ether

Sources & evidence

ORD record
ord-55f37855c3b14d9cbf67c2a4b55f615d
Source dataset
uspto-grants-1982_12
Patent number
US04362666

Reaction notes

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