89573-00-2 → 4-{N-[alpha-(4-Methyl-phenyl)-2-piperidino-benzyl]-aminocarbonylmethyl}-benzaldehyde

Participants

Reaction Conditions

Reaction Steps

Quantities of 8.85 gm (20 m mol) of 4-{N-[α-(4-Methylphenyl)-2-piperidino-benzyl]-aminocarbonylmethyl}-benzoic acid and 3.25 gm (20 m mol) of N,N'-carbonyldiimidazole were refluxed in 100 ml of absolute tetrahydrofuran for two hours. Then, the mixture was concentrated by evaporation, and, after addition of 50 ml of pyridine and 3.7 gm (20 m mol) of 4-toluene-sulphonic acid hydrazide, the mixture was refluxed for a further two hours. The mixture was then poured onto ice water and subjected to suction filtration, and the precipitate was dried. The resulting crude toluene-sulphonic acid hydrazide of the carboxylic acid used was mixed with 20 gm of anhydrous sodium carbonate and heated to 170° C. in 50 ml of ethylene glycol for two hours. Then, it was added to water and extracted with chloroform. The concentrated extracts were purified by column chromatography on silica gel by use of toluene/ethyl acetate (5:1) as eluant.

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