Hydrochloric Acid → 6-Chloro-2-{3,3,3-trifluoro-2-[3-(3-trifluoromethyl-phenyl)-piperidin-1-ylmethyl]-propyl}-benzooxazole hydrochloride

Participants

Reaction Conditions

Reaction Steps

In a 5 mL microwave vial, 4,4,4-trifluoro-3-((3-(3-(trifluoromethyl)phenyl)piperidin-1-yl)methyl)butanoic acid (50 mg, 130 μmol), 2-amino-5-chlorophenol (28.1 mg, 196 μmol) and p-toluenesulfonic acid (4.96 mg, 26.1 μmol) were combined in toluene (1.00 ml) to give a dark brown suspension. The tube was sealed and heated in a microwave at 135° C. for 2 h, diluted with ethyl acetate (30 ml), washed with a saturated solution of Na2CO3 (30 ml) and H2O (30 ml), dried over MgSO4, filtered and concentrated in vacuo to give an oil. The oil was purified on a silica column (100% CH2Cl2 to 50% ethyl acetate/CH2Cl2 gradient) to afford an oil which was dissolved in ether/hexane (1 ml/1 ml), treated with a 4N HCl solution in dioxanes (0.02 ml) and concentrated to afford 25 mg (37%) of 6-chloro-2-{3,3,3-trifluoro-2-[3-(3-trifluoromethyl-phenyl)-piperidin-1-ylmethyl]-propyl}-benzooxazole hydrochloride as a light red solid. MH+=491.

Provenance & Evidence