1-Methylpiperazine → 3-methoxy-4-nitro-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-ylcarbonyl)pent-1-yloxy]phenyl]benzamide

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Reaction Steps

3-Methoxy-4-nitro-N-[2-(5-carboxypent-1-yloxy)-4-methylphenyl]-N-methylbenzamide (5.2 g), 1-methylpiperazine (1.45 g) and 1-hydroxybenzotriazole (1.96 g) were dissolved in N,N-dimethylformamide (50 ml) and the solution was cooled in an ice bath. To the mixture was added N-ethyl-N'-(3-dimethylaminopropyl)-carbodiimide hydrochloride (2.78 g) and the solution was stirred at the same temperature for 30 minutes. The reaction mixture was allowed to warm to ambient temperature and stirring was continued for additional 20 hours. The reaction mixture was diluted with ethyl acetate and the solution was washed successively with saturated sodium hydrogen carbonate and brine, and dried over sodium sulfate. The sodium sulfate was removed and the solvent was removed by evaporation to give oil. The crude material was subjected to a silica gel column chromatography (SiO2 ; 120 g, 2% methanol in chloroform) to give 3-methoxy-4-nitro-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-ylcarbonyl)pent-1-yloxy]phenyl]benzamide (6.2 g).

Provenance & Evidence