Reaction #4128

Reaction equation

N-bromosuccinimide

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

dichloromethane

→

product

Yield 11.6%

10-Bromo-9-methyl-6-(4-methyl-1-piperazinyl)-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine

Yield 11.6%

Solvents

dimethylformamide

dimethylformamide

Conditions

Workup

1. 1
   Washwas washed with brine (4 times, 150 ml)
2. 2
   Dryingdried over anhydrous magnesium sulfate
3. 3
   OtherThe solvent was removed at reduced pressure
4. 4
   Otherthe residue was dried
5. 5
   OtherPurification
6. 6
   Washeluted with dichloromethane (500 ml) and 2% methanol in dichloromethane (250 ml)
7. 7
   workup.ADDITIONThe fractions containing the product
8. 8
   Concentrationconcentrated
9. 9
   OtherRecrystallization from 2-propanol:water (1:1, 20 ml)

Procedure

A solution of N-bromosuccinimide (0.91 g, 5.1 mmoles) in dimethylformamide (3 ml) was added dropwise to a solution of 6-(4-methyl-1-piperazinyl)-9-methyl-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine (1.6 g, 4.8 mmoles) in dimethylformamide (30 ml) at 0°-3° C. The reaction mixture was stirred for 30 minutes. The solution was poured into dichloromethane (250 ml), and was washed with brine (4 times, 150 ml), and dried over anhydrous magnesium sulfate. The solvent was removed at reduced pressure and the residue was dried. Purification was accomplished by flash chromatography on an aluminium oxide column (grade III, 60 g), eluted with dichloromethane (500 ml) and 2% methanol in dichloromethane (250 ml). The fractions containing the product were pooled and concentrated. Recrystallization from 2-propanol:water (1:1, 20 ml) yielded 230 mg (11.6%) of product, mp 177°-177° C.

Source