Réaction #4196

Équation de réaction

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

→

product

Rendement 79.0%

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

Rendement 79.0%

Solvants

phosphorus oxychloride

Conditions de réaction

Traitement

1. 1
   Températurewas heated
2. 2
   Températureunder reflux under nitrogen for 5 hours
3. 3
   Autreexcess phosphorous oxychloride was removed at aspirator pressure
4. 4
   Températurewith heating
5. 5
   TempératureThe 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
   Autrethe organic phase was separated
8. 8
   Lavagewashed with 2N sodium hydroxide solution, twice with water
9. 9
   Séchagedried over anhydrous sodium sulfate
10. 10
    Concentrationconcentrated in vacuo

Mode opératoire

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.

Source