Hydrochloric Acid → 1-{2-[5-(4-Chloro-phenyl)-[1,3,4]oxadiazol-2-ylmethyl]-3,3,3-trifluoro-propyl}-3-(3-trifluoromethyl-phenyl)-piperidine hydrochloride

関与物質

反応条件

反応手順

To a round-bottomed flask (5 ml) was added 4,4,4-trifluoro-3-((3-(3-(trifluoromethyl)phenyl)-piperidin-1-yl)methyl)butanoic acid (50 mg, 130 μmol), 4-chlorobenzohydrazide (22.3 mg, 130 μmol,) and POCl3 (1.64 g, 1 mL, 10.7 mmol). The reaction mixture was heated to reflux at 110° C. for 4 hr. The crude reaction mixture was allowed to cool to room temperature, poured into ice/water and made basic with a saturated solution of Na2CO3. The reaction mixture was extracted with ethyl acetate, washed with brine and H2O, dried over MgSO4, filtered and concentrated. The resultant residue was purified on a silica column (100% CH2Cl2 to 40% ethyl acetate/CH2Cl2 eluent) to give an oil. The oil was dissolved in ether/hexane, treated with 4N HCl in dioxane (0.2 ml) and concentrated to afford 40 mg (56%) of 1-{2-[5-(4-chloro-phenyl)-[1,3,4]oxadiazol-2-ylmethyl]-3,3,3-trifluoro-propyl}-3-(3-trifluoromethyl-phenyl)-piperidine hydrochloride as a white solid. MH+=518.

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