4-Bromo-6-(4-methyl-1-piperazinyl)-9-methyl-1,2-dihydrobenzo[b]-pyrrolo [3,2,1-jk][1,4]benzodiazepine → 4-Bromo-6-(4-methyl-1-piperazinyl)-9-methylbenzo[b]pyrrolo-[3,2,1-jk][1,4]benzodiazepine

HRID 978288

Reaktionsgleichung

Reaktionsgleichung von HRID 978288
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:13][CH2:12][N:11]3[C:5]2=[C:6]([CH:26]=1)[C:7]([N:19]1[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]1)=[N:8][C:9]1[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][C:10]=13>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[Br:1][C:2]1[CH:3]=[C:4]2[CH:13]=[CH:12][N:11]3[C:5]2=[C:6]([CH:26]=1)[C:7]([N:19]1[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]1)=[N:8][C:9]1[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][C:10]=13

Komponenten

4

Edukt 1

HCID 138233144-Bromo-6-(4-methyl-1-piperazinyl)-9-methyl-1,2-dihydrobenzo[b]-pyrrolo [3,2,1-jk][1,4]benzodiazepine

Produkt 1

HCID 138233084-Bromo-6-(4-methyl-1-piperazinyl)-9-methylbenzo[b]pyrrolo-[3,2,1-jk][1,4]benzodiazepineAusbeute 42,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418406HCID 178418406, VerbindungKatalysatorHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a solution of 4-bromo-6-(4-methyl-1-piperazinyl)-9-methyl-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine (5.7 g, 13.8 mmoles) in chloroform (540 ml) was added manganese dioxide (25 gm), and the mixture was heated under reflux for 4 days. The mixture was filtered, and the filter cake washed with dichloromethane. The filtrate was concentrated under vacuum. The residue was purified on a silica gel column, eluted with 2% methanol/dichloromethane. The fractions (75-100 ml each) containing pure product were pooled and concentrated. Recrystallization from a small volume of 2-propanol yielded 2.41 g (42%) of product, mp 153°-155° C.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 days
  3. filtrationThe mixture was filtered
  4. washthe filter cake washed with dichloromethane
  5. concentrationThe filtrate was concentrated under vacuum
  6. customThe residue was purified on a silica gel column
  7. washeluted with 2% methanol/dichloromethane
  8. additionThe fractions (75-100 ml each) containing pure product
  9. concentrationconcentrated
  10. customRecrystallization from a small volume of 2-propanol

Quellen und Nachweise

ORD-Eintrag
ord-8c5a3f95d4184a32bed230d25ba2ea11
Quelldatensatz
uspto-grants-1987_05
Patentnummer
US04663453

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