Reacción #4169

Ecuación de reacción

9-methyl-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepin-6-one

4-methylpiperidine

→

9-Methyl-6-(4-methyl-1-piperidinyl)-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas heated under nitrogen until a solution
2. 2
   Otroresulted
3. 3
   TemperaturaThe mixture was heated
4. 4
   Temperaturaunder reflux for three hours
5. 5
   Filtraciónfiltered
6. 6
   Otrothe layers were separated
7. 7
   ExtracciónThe aqueous phase was extracted with 250 ml of toluene
8. 8
   Lavadowashed once with 2N sodium hydroxide solution, twice with water
9. 9
   Secadodried over anhydrous sodium sulfate
10. 10
    Filtraciónfiltered
11. 11
    Concentraciónconcentrated in vacuo to 8.1 g (98%) of product
12. 12
    OtroRecrystallization from ethyl acetate
13. 13
    Otroprovided the analytical sample, mp 194°-196° C.

Procedimiento

A stirred mixture of 6.26 g (0.0250 mole) of 9-methyl-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepin-6-one and 1000 ml of toluene was heated under nitrogen until a solution resulted. Then there was added 24.8 g (0.250 mole) of 4-methylpiperidine, followed by 14.2 g (0.075 mole) of titanium tetrachloride. The mixture was heated under reflux for three hours, cooled to room temperature and filtered. The filtrate was stirred with 500 ml of 2N sodium hydroxide solution for 15 minutes and the layers were separated. The aqueous phase was extracted with 250 ml of toluene. The toluene layers were combined, washed once with 2N sodium hydroxide solution, twice with water, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to 8.1 g (98%) of product. Recrystallization from ethyl acetate provided the analytical sample, mp 194°-196° C.

Fuente