Reaction #63395

Reaction equation

4-chloro-6-(4-methyl-1-piperazinyl)-1,2,dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine

→

product

Yield 63.7%

4-Chloro-6-(4-methyl-1-piperazinyl)benzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine

Yield 63.7%

Solvents

chloroform

Conditions

Workup

1. 1
   TemperatureThe mixture was heated
2. 2
   Temperatureunder reflux for 24 hours
3. 3
   TemperatureThe mixture was cooled
4. 4
   Filtrationfiltered
5. 5
   Washthe solid was washed with dichloromethane (200 ml)
6. 6
   ConcentrationThe filtrate was then concentrated to dryness
7. 7
   OtherThe residue was purified by flash chromatography over a silica gel column (150 g)
8. 8
   Washeluted with 2% methanol in dichloromethane (4 l) and 3% methanol in dichloromethane 2 l)
9. 9
   OtherEvaporation of the eluent

Procedure

To a solution of 4-chloro-6-(4-methyl-1-piperazinyl)-1,2,dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine (6 g, 17 mmoles), in chloroform (150 ml) was added manganese dioxide (10.5 g). The mixture was heated under reflux for 24 hours. The mixture was cooled, filtered and the solid was washed with dichloromethane (200 ml). The filtrate was then concentrated to dryness. The residue was purified by flash chromatography over a silica gel column (150 g), eluted with 2% methanol in dichloromethane (4 l) and 3% methanol in dichloromethane 2 l). Evaporation of the eluent gave 3.8 g (63%) of product. Recrystallization from toluene (40 ml) yielded the analytical sample, mp 170°-172° C.

Source