Acetic Acid → HCID 69432244, compound

Participants

Reaction Steps

Under nitrogen, the N-benzyl-N-[cis-3-[(4-methyl-1H-indazol-5-yl)oxy]cyclohexyl]amine (150 mg, 0.447 mmol) obtained in Example 716 and 36%-formaldehyde (56 mg, 0.671 mmol) were suspended in methanol (5 ml), followed by adding thereto acetic acid (0.2 ml), and the resulting mixture was stirred at room temperature for 30 minutes. Then, sodium cyanoborohydride (56 mg, 0.894 mmol) was added thereto and the resulting mixture was stirred at room temperature for 17 hours. The reaction mixture was diluted with chloroform and then separated by the addition of a 1N-aqueous sodium hydroxide solution, and the desired compound was further extracted from the aqueous layer with chloroform. The combined chloroform layer was washed with a saturated aqueous sodium chloride solution, dried by the addition of anhydrous magnesium sulfate, and then filtered. The solvent was distilled off under reduced pressure and the resulting concentration residue was purified by a silica gel column chromatography (eluent: acetonitrile/aqueous ammonia=100/0, 100/1) to obtain N-benzyl-N-methyl-N-[cis-3-[(4-methyl-1H-indazol-5-yl)oxy]cyclohexyl]amine (136 mg, yield 87.0%) as a white amorphous substance.

Provenance & Evidence