N-[2-(5-bromo-1-indolinyl)-5-methylphenyl]-4-methyl-1-piperazinecarboxamide → 4-Bromo-6-(4-methyl-1-piperazinyl)-9-methyl-1,2-dihydrobenzo[b]-pyrrolo [3,2,1-jk][1,4]benzodiazepine

HRID 34378

Reaktionsgleichung

Reaktionsgleichung von HRID 34378
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:12]=1[NH:18][C:19]([N:21]1[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]1)=O)[CH2:6][CH2:5]2>P(Cl)(Cl)(Cl)=O>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:5][CH2:6][N:7]3[C:8]2=[C:9]([CH:10]=1)[C:19]([N:21]1[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]1)=[N:18][C:12]1[CH:13]=[C:14]([CH3:17])[CH:15]=[CH:16][C:11]=13

Komponenten

3

Edukt 1

HCID 13823367N-[2-(5-bromo-1-indolinyl)-5-methylphenyl]-4-methyl-1-piperazinecarboxamide

Produkt 1

HCID 138233144-Bromo-6-(4-methyl-1-piperazinyl)-9-methyl-1,2-dihydrobenzo[b]-pyrrolo [3,2,1-jk][1,4]benzodiazepineAusbeute 53,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24813Phosphorus oxychlorideLösungsmittel

Versuchsvorschrift

A solution of N-[2-(5-bromo-1-indolinyl)-5-methylphenyl]-4-methyl-1-piperazinecarboxamide (3.3 g, 7.68 mmoles) and phosphorus oxychloride (30 ml) was heated at reflux for 25 minutes under nitrogen. The solution was cooled and excess phosphorus oxychloride was removed at 55°-60° C. under vacuum. Ice-chilled 2N-sodium hydroxide solution (100 ml) and dichloromethane (250 ml) were added to the residue. The organic phase was separated and washed with brine (2 times, 100 ml), dried over anhydrous magnesium sulfate, and concentrated. Purification was accomplished by flash chromatography over aluminum oxide (Grade III, 100 g), eluted with dichloromethane (21). The fractions containing pure material were pooled and concentrated. Recrystallization from isopropanol (30 ml) yielded 1.7 g (53.9%) of product, mp 187°-189° C.

Aufarbeitung

  1. temperatureat reflux for 25 minutes under nitrogen
  2. temperatureThe solution was cooled
  3. customexcess phosphorus oxychloride was removed at 55°-60° C. under vacuum
  4. temperatureIce-chilled 2N-sodium hydroxide solution (100 ml) and dichloromethane (250 ml)
  5. additionwere added to the residue
  6. customThe organic phase was separated
  7. washwashed with brine (2 times, 100 ml)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated
  10. customPurification
  11. washeluted with dichloromethane (21)
  12. additionThe fractions containing pure material
  13. concentrationconcentrated
  14. customRecrystallization from isopropanol (30 ml)

Quellen und Nachweise

ORD-Eintrag
ord-e758e2b4f0dd4afa9aa1ddd3a29ae6e2
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04761412

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