N-[3-(4-Methylpiperazin-1-yl)propyl]-2-nitroaniline → HCID 14319495, compound

Participants

Reaction Conditions

Reaction Steps

To a mechanically stirred solution of stannous chloride (1060 g., 4.71 mole) in concentrated hydrochloric acid (1200 ml.), under nitrogen, was added a solution of 2-[3-(4-methyl-1-piperazinyl)propylamino]nitrobenzene (438 g., 1.57 mole) in conc. HCl (800 ml.) at a rate sufficient to maintain the reaction temperature at 55°-60° C. The addition took place over about 1.5 hours. The heavy white precipitate which formed during the course of the addition, was stirred for an additional 1 hour. The reaction mixture was then filtered and the resultant white solid was dissolved in 3 liters of water. An equal volume of chloroform was added, the mixture was cooled to 5° C. and adjusted to pH 10, with 50% KOH. The organic layer was separated, and the cold basic aqueous phase extracted again with chloroform (1l). The organic layers were combined, dried (MgSO4) and evaporated in vacuo to give 334.8 g. of N-[3-(4-methyl-1-piperazinyl)propyl]-o-phenylenediamine as a brown oil (yield 97%). A small amount of the oil was triturated with hexane. The hexane layer was cooled to 5° C. forming a tan solid which on recrystallization from benzene-hexane give an analytical sample, m.p. 65°-67° C.

Provenance & Evidence