Hydrochloric Acid → Cyclohexanecarboxylic acid (2-chloro-4-hydroxy-benzyl)-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amide, hydrochloride salt

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A solution of cyclohexanecarboxylic acid [2-chloro-4-(tetrahydro-pyran-2-yloxy)-benzyl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amide (2.0 g) in 3:1 ethanol:1N HCl (40 mL) was stirred at room temperature for 1.5 hr. Saturated aqueous sodium bicarbonate solution was added and the aqueous solution was washed with methylene chloride. The organic solution was dried (magnesium sulfate), filtered and concentrated in vacuo. The crude product was purified by Biotage® chromatography (methylene chloride to 4% methanol/methylene chloride). The resulting white solid (1.53 g) was suspended in methanol (20 mL) and 4M HCl in dioxane was added. The mixture was stirred at room temperature for 1 hr. and was concentrated in vacuo to yield the title compound as a tan solid (1.60 g). MS 317.2 (MH+−40)

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