Methane → 5,10-Dihydro-5-{[(4-methyl-1-piperazinyl)amino]carbonyl}-11H-dibenzo[b,e][1,4]diazepin-11-one

HRID 325882Notes

Reaction equation

HRID 325882 reaction equation
Cl[C:2]([N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:8](=[O:15])[NH:7][C:6]2[CH:16]=[CH:17][CH:18]=[CH:19][C:5]1=2)=[O:3].[NH2:20][N:21]1[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]1.C>O1CCOCC1>[CH3:27][N:24]1[CH2:25][CH2:26][N:21]([NH:20][C:2]([N:4]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[C:8](=[O:15])[NH:7][C:6]3[CH:16]=[CH:17][CH:18]=[CH:19][C:5]2=3)=[O:3])[CH2:22][CH2:23]1

Participants

5

Reactant 3

HCID 297MethaneHCID 813491-Amino-4-methylpiperazineHCID 132767455-chlorocarbonyl-5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one

Product 1

HCID 132767475,10-Dihydro-5-{[(4-methyl-1-piperazinyl)amino]carbonyl}-11H-dibenzo[b,e][1,4]diazepin-11-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5.5 gm (0.0202 mol) of 5-chlorocarbonyl-5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one, 8.6 gm (0.075 mol) of 1-amino-4-methylpiperazine, and 200 ml of anhydrous dioxane was heated for 30 minutes over a steam bath. Then, 2 gm of active charcoal were added to the resulting cloudy reaction mixture while it was still hot, the mixture was filtered, and the filtrate obtained was concentrated by evaporation in vacuo. The residue was purified by column chromatography on 300 gm of silica gel [eluant: dichloromethane/methanol/conc. aqueous ammonia mixture (volume ratio of 800:200:5)]. The residue remaining after the eluates had been concentrated was taken up in 500 ml of ethyl acetate, 1 gm of active charcoal was added, and the resulting mixture was boiled, filtered, and concentrated by evaporation. Then, 300 ml of methanol were added, and the resulting mixture was filtered while hot and evaporated to dryness. After recrystallization from ethanol, 1.8 gm (25% of theory) of colorless crystals were obtained, m.p.: 213°-214° C. (D).

Workup

  1. temperaturewas heated for 30 minutes over a steam bath
  2. filtrationthe mixture was filtered
  3. customthe filtrate obtained
  4. concentrationwas concentrated by evaporation in vacuo
  5. customThe residue was purified by column chromatography on 300 gm of silica gel [eluant: dichloromethane/methanol/conc. aqueous ammonia mixture (volume ratio of 800:200:5)]
  6. concentrationhad been concentrated
  7. addition1 gm of active charcoal was added
  8. filtrationfiltered
  9. concentrationconcentrated by evaporation
  10. additionThen, 300 ml of methanol were added
  11. filtrationthe resulting mixture was filtered while hot and
  12. customevaporated to dryness
  13. customAfter recrystallization from ethanol, 1.8 gm (25% of theory) of colorless crystals
  14. customwere obtained

Sources & evidence

ORD record
ord-4d0c63c7f22c436ebfbbc083841ebae3
Source dataset
uspto-grants-1984_04
Patent number
US04443452

Reaction notes

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