Hydrochloric Acid → Methyl 3-(3-cyanophenyl)-5-[(piperidin-4-ylmethyl)aminomethyl]benzoate

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Reaction Steps

In 30 ml of toluene, were dissolved 3.00 g of the compound obtained in Example 11 and 1.50 g of 4-aminomethylpiperidine. The resulting solution was refluxed for 3 hours to remove the produced water. The solvent was evaporated from the reaction solution under reduced pressure, and 10 ml of tetrahydrofuran and 20 ml of methanol were added to the residue to provide a solution. To the resulting solution, was added 0.500 g of sodium borohydride under cooling with ice. The mixture was stirred at this temperature for 1 hour, then returned to room temperature and stirred for another hour. To the resulting solution was added a 1 M hydrochloric acid to quench the reaction. The resulting solution was washed with ethyl acetate. A 1 M aqueous solution of sodium hydroxide was added to the obtained aqueous layer until the pH attained 10. The resulting solution was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine and subsequently dried over sodium sulfate, and the solvent was removed under reduced pressure to provide 2.9 g (71%) of the title compound as an oil.

Provenance & Evidence