Hydrochloric Acid → 4-{3-[4-(3-{4-[amino(imino)methyl]phenoxy}propyl)-1-piperidinyl]propoxy}-N'-hydroxybenzamidine

Participants

Reaction Steps

To an ethanol (5 mL) suspension of 0.50 g of tert-butyl=[1-amino-1-(4-{3-[1-(3-{4-[amino(hydroxyimino)methyl]phenoxy}propyl)-4-piperidinyl]propoxy}phenyl)methylidene]carbamate was added 1 mL of hydrochloric acid at room temperature, which was then stirred at the same temperature for 15 hours and 30 minutes. To the reaction mixture was added 4 mL of hydrochloric acid at room temperature, which was then stirred at the same temperature for 2 hours and 30 minutes. The solvent was distilled off under reduced pressure, and water was then added, followed by adjustment to pH 12.5 using a 5 mol/L sodium hydroxide aqueous solution. The precipitate was collected by filtration and washed with water. The resultant solid was dissolved in 1 mol/L hydrochloric acid, followed by distilling off the solvent under reduced pressure before purification using silica gel column chromatography (silica gel: ODS-A from YMC, eluent; water:ethanol=95:5). The eluate was concentrated to about 20 mL, which was then adjusted to pH 12.5 using a 5 mol/L sodium hydroxide aqueous solution. The precipitate was collected by filtration and washed with water to provide 0.17 g of 4-{3-[4-(3-{4-[amino(imino)methyl]phenoxy}propyl)-1-piperidinyl]propoxy}-N′-hydroxybenzamidine as white solid form.

Provenance & Evidence