Sodium Bicarbonate → HCID 14837053, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 10 g of sodium bicarbonate, 0.12 g of potassium iodide, 5.0 g of 4-(2,3,4,5,6-pentafluorophenoxy)piperidine and 75 ml of dimethylformamide was treated with a solution of 5.37 g of 3-(3-chloropropyl)-5,6-dimethoxy-1,2-benzisoxazole in 25 ml dimethylformamide and stirred for five hours at 70° C. The reaction mixture was filtered and the filtrate poured into water and extracted with ethyl acetate. The organic layer was washed with water followed by a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. After filtering, evaporation under reduced pressure afforded a residue which was purified by means of high pressure liquid chromatography (silica gel; elution with ethyl acetate) to yield 5.5 g of 1-[(5,6-dimethoxy-1,2-benzisoxazol-3-yl)propyl]-4-(2,3,4,5,6-pentafluorophenoxy)piperidine as a waxy solid. This material was dissolved in isopropanol and acidified to pH 1 with etheral hydrogen chloride to precipitate the corresponding hydrochloride salt. Recrystallization from isopropanol afforded 3.3 g (36%) of 1-[(5,6-dimethoxy- 1,2-benzisoxazol-3-yl)propyl]-4-(2,3,4,5, 6-pentafluorophenoxy)piperidine hydrochloride, m.p. 210°-212° C.

Provenance & Evidence