Sodium triacetoxyborohydride → HCID 66703871, compound

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4-Chloro-N-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)-2-[(piperidin-2-ylmethyl)amino]benzamide hydrochloride (100 mg) was dissolved in a mixed solution of acetic acid (3 mL) and methanol (2 mL), and 1 ml of formaldehyde aqueous solution (36%) was added thereto. Sodium triacetoxyborohydride (252 mg) was added to this solution at 0° C., followed by stirring at room temperature for 30 minutes. After concentration under a reduced pressure, this was made basic by adding a saturated sodium bicarbonate aqueous solution, followed by extraction with chloroform. After drying the organic layer with magnesium sulfate, the solvent was evaporated under a reduced pressure. By purifying the residue by silica gel column chromatography (chloroform:methanol, 10:1) and treating the resulting free base with 4 M hydrogen chloride/ethyl acetate solution, 4-chloro-N-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)-2-{[(1-methylpiperidin-2-yl)methyl]amino}benzamide hydrochloride (45 mg) was obtained as a solid.

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