Toluene → HCID 12617933, compound

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Reaction Steps

A mixture of 2 g. of 5,10-dihydro-11H-pyrrolo[2,1-c]-[1,4]benzodiazepin-11-one (Example 1), 2 g. of phosphorus pentachloride and two drops of N,N-dimethylformamide in 50 ml. of toluene is heated on the steam bath for several hours. The solvent is removed by distillation, 25 ml. of chloroform is added and the mixture evaporated again. The residue is dissolved in 25 ml. of chloroform and this solution slowly added to 10 ml. of N-methylpiperazine in 40 ml. of toluene. This mixture is heated for several hours, finally to the boiling point of toluene, and then evaporated to an oily residue. The residue is taken up in ether (500 ml) and extracted into dilute acetic acid. The aqueous acetic acid layer is made basic with concentrated ammonium hydroxide and the product which precipitates is extracted into ether. The ether solution is dried over anhydrous potassium carbonate, and evaporated to a residue which contains the desired product. When purified by recrystallization it shows m.p. 139°-141° C. (base).

Provenance & Evidence