1-(3-BUTOXYPROPYL) PIPERIDIN-4-ONE AS A SYNTHONE OF PIPERASINE-SUBSTITUTED DERIVATIVES OF BISPIDINE

Abstract

To search for novel biologically active compoundsof a bispidine family, piperazinesubstituted 3,7-diazabicyclo[3.3.1]nonanes based on 1- (3-butoxypropyl) piperidin-4-one had been synthesized. Mannich reaction is a convenient one-step method for the synthesis of bispidinones. Thus, 3-(3-butoxypropyl)-7-[(2-(piperazin-1-yl)ethyl)]-3,7-diazabicyclo[3.3.1]nonan-9-one was synthesized via simultaneous condensation of piperidone with paraform and 2-(piperazin-1-yl)ethylaminein acetic-methanol medium. Further, the corresponding nonane was obtained with a yield of 77% via reduction of 3,7-diazabicyclo[3.3.1]nonan-9-one by the action of hydrazine hydrate in triethylene glycol in the presence of KOH under the conditions of the Wolff-Kishner reaction. Prolonged boiling (for 8-10 hours)of3,7-diazabicyclo[3.3.1]nonan-9-one with hydroxylamine hydrochloride led to the target oxime with a yield of 43%.To obtain a prodrug, by reacting the oxime 3-(3-butoxypropyl)-7-[(2-(piperazin-1-yl)ethyl)]-3,7-diazabicyclo[3.3.1]nonan-9-one with benzoyl chloride in absolute benzene at room temperature, followed by processing the resulting hydrochloride with potash, its O-benzoyloxime was obtained. The composition and structure of synthesized compounds were confirmed by data of elemental analysis, thin layer chromatography, IR and 13C NMR spectroscopies.

References

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