Reaktion #4138

Reaktionsgleichung

4-methyl-N-[2-(6-bromo-1,2,3,4-tetrahydro-1-quinolinyl)phenyl]piperazine-carboxamide

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product

Ausbeute 79.0%

5-Bromo-7-(4-methyl-1-piperazinyl)-2,3-dihydro-1H-quino[1,8-ab][1,5]benzodiazepine

Ausbeute 79.0%

Lösungsmittel

phosphorus oxychloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturunder reflux under nitrogen for 5 hours
3. 3
   Sonstigeexcess phosphorous oxychloride was removed at aspirator pressure
4. 4
   Temperaturwith heating
5. 5
   TemperaturThe residue was chilled in an ice-bath (with exclusion of moisture)
6. 6
   workup.ADDITIONtreated with ice-cold 2N sodium hydroxide solution (250 ml) and dichloromethane (500 ml)
7. 7
   Sonstigethe organic phase was separated
8. 8
   Waschenwashed with 2N sodium hydroxide solution, twice with water
9. 9
   Trocknendried over anhydrous sodium sulfate
10. 10
    Einengenconcentrated in vacuo

Vorschrift

A stirred mixture of 4-methyl-N-[2-(6-bromo-1,2,3,4-tetrahydro-1-quinolinyl)phenyl]piperazine-carboxamide (14.2 g, 0.0330 mole) in phosphorus oxychloride (250 ml) was heated under reflux under nitrogen for 5 hours. The reaction mixture was cooled to room temperature and excess phosphorous oxychloride was removed at aspirator pressure with heating. The residue was chilled in an ice-bath (with exclusion of moisture), and treated with ice-cold 2N sodium hydroxide solution (250 ml) and dichloromethane (500 ml). The mixture was stirred, the organic phase was separated, washed with 2N sodium hydroxide solution, twice with water, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was digested in boiling methanol (40 ml) to afford 10.7 g (79%) of product. Recrystallization from ethanol provided the analytical sample, mp 181°-183° C.

Quelle