Methane → HCID 20475065, compound

HRID 2295278Notes

Reaction equation

HRID 2295278 reaction equation
[Cl:1][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]=[N: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>[OH2:3].[ClH:1].[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]=[N:19][C:5]2=3)=[O:3])[CH2:22][CH2:23]1

Participants

5

Reactant 3

HCID 297MethaneHCID 813491-Amino-4-methylpiperazineHCID 1104396211-chlorocarbonyl-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

Product 1

HCID 20475065HCID 20475065, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5.5 g (0.0201 mol) of 11-chlorocarbonyl-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one, 6.9 g (0.06 mol) of 1-amino-4-methylpiperazine and 150 ml of anhydrous dioxane was heated for 30 minutes over a steam bath and the cloudy reaction mixture obtained was then mixed while still hot with 2 g of active charcoal, then filtered and the filtrate obtained was concentrated by evaporation in vacuo. The residue was purified by column chromatography on 300 g of silica gel, using a mixture of dichloromethane, methanol and conc. aqueous ammonia (ratio by volume 800:200:5). The residue remaining after the eluates of interest had been evaporated was recrystallized from ethanol. 1.5 g (19% of theory) of colorless crystals of 5,11-dihydro-11-[[(4-methyl-1-piperazinyl)amino]-carbonyl]-6H-pyrido[2,3-b]-[1,4]benzodiazepin-6-one hydrochloride hydrate was obtained,

Workup

  1. temperaturewas heated for 30 minutes over a steam bath
  2. customthe cloudy reaction mixture
  3. customobtained
  4. filtrationfiltered
  5. customthe filtrate obtained
  6. concentrationwas concentrated by evaporation in vacuo
  7. customThe residue was purified by column chromatography on 300 g of silica gel
  8. additiona mixture of dichloromethane, methanol and conc. aqueous ammonia (ratio by volume 800:200:5)
  9. customhad been evaporated
  10. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-ca8e9eb52080477380a092a0d672e351
Source dataset
uspto-grants-1984_01
Patent number
US04424222

Reaction notes

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