1-Phenylpiperazine → 9-Bromo-6-(4-phenyl-1-piperazinyl)-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine

A stirred mixture of 7.88 g (0.0250 mole) of 9-bromo-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine-6-one and 1200 ml of toluene was heated under nitrogen until a solution resulted. Then there was added 40.6 g (0.250 mole) of N-phenylpiperazine, 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 treated with 500 ml of 2N sodium hydroxide solution. After stirring vigorously for 15 minutes, the layers were separated. The aqueous phase was extracted with 300 ml of toluene. The toluene layers were combined, washed once with 2N sodium hydroxide solution, twice with water, dried over anhydrous sodium sulfate, and concentrated to an oil. The oil was taken up in 80 ml of hot methanol, from which the product crystallized, affording 7.8 g (68%) of product. Recrystallization from a hot solution of dichloromethane (25 ml), to which methanol (25 ml) was added, provided the analytical sample, mp 171°-173° C.

1. temperaturewas heated under nitrogen until a solution
2. customresulted
3. temperatureThe mixture was heated
4. temperatureunder reflux for three hours
5. customthe layers were separated
6. extractionThe aqueous phase was extracted with 300 ml of toluene
7. washwashed once with 2N sodium hydroxide solution, twice with water
8. dry with materialdried over anhydrous sodium sulfate
9. concentrationconcentrated to an oil
10. customcrystallized

ORDレコード

ord-242c4d5ab06745cab99e5588071de23e

出典データセット

uspto-grants-1988_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04723007