Hydrochloric Acid → Cyclohexanecarboxylic Acid (4-hydroxy-benzyl)-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amide

Participants

Reaction Steps

A mixture of cyclohexanecarboxylic acid [4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-[4-(tetrahydro-pyran-2-yloxy)-benzyl]-amide (1.64 g, 3.24 mmol), pyridinium p-toluenesulfonate (85 mg, 0.32 mmmol) and ethanol (30 mL) was stirred at room temperature for 24 hr. Aqueous 1N HCl (10 mL) was added and the reaction was stirred for 3–4 hr. The reaction mixture was concentrated to 1/3 the volume and saturated aqueous sodium bicarbonate was added. The aqueous solution was washed with methylene chloride and the organic solution was dried (magnesium sulfate), filtered, and concentrated. Medium pressure chromatography using a solvent gradient (3% methanol in methylene chloride to 15% methanol in methylene chloride) provided the title compound as a white solid (1.16 g). The solid was suspended in methanol (15 mL) and 1.4 mL of 4N HCl in dioxane was added dropwise. The reaction was stirred at room temperature for 0.5 hr. and was concentrated to provide the title compound as the hydrochloride salt. MS 423.2 (M+1)+

Provenance & Evidence