Hydrochloric Acid → HCID 68519802, compound

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Reaction Steps

Combine the compound of Example 48 and sodium perborate (162 mg, 1.62 mmol) in acetic acid (4 mL). After 2 days, add dichloromethane (20 mL) and water (5 mL). Separate the layers, wash the organic layer with saturated aqueous NaHCO3 (10 mL), brine (10 mL), dry with MgSO4, filter, and concentrate in vacuo. Chromatograph the residue on a SiO2 column eluting the 6-(4-methanesulfonyl-3-methyl-phenyl)-5-[4-(2-piperidin-1-yl-ethoxy)-phenoxy]-naphthalen-2-ol with a step gradient of methanol in dichloromethane (0 to 5%). Dissolve the free base in diethyl ether (5.0 mL), ethyl acetate (6.0 mL) and methanol (1.0 mL) and add 2M HCl in diethyl ether (1 mL, 2.0 mmol). Collect the precipitate on filter paper, rinse with diethyl ether and dry in vacuo (<2 mm of Hg) at 65° C. for 48 hours to give 40 mg of the title compound (11%): mass spectrum (ion spray): m/z=537.0 (M+H—HCl).

Provenance & Evidence