Sodium Iodide → HCID 18959738, compound

Participants

Reaction Steps

A mixture of 6-(6-chlorohexoxy) flavone (Prepared from 6-hydroxyflavone and 1-bromo-6-chlorohexane by a manner similar to 6-(4-chlorobutoxy) flavone described in Example 1.) (2.00 g, 5.6 mmol), 4-(2-hydroxyethyl)piperidine (1.09 g, 8.4 mmol), sodium iodide (0.92 g, 6.1 mmol), and potassium carbonate (1.16 g, 8.4 mmol) in anhydrous DMF was stirred at 80°-90° C. for 24 hours. The reaction was cooled to room temperature and water (300 mL) was added to the flask. The resulting precipitate was collected by filtration and dissolved in methylene chloride (350 mL). This solution was washed with water (2×150 mL), brine (2×150 mL) and then the solution was dried over sodium sulfate. Removal of the solvent gave 2.32 g of the free base. The free base was dissolved in hot EtOAc and the solution filtered. Then 1 equivalent of a 1 M anhydrous solution of HCl in ether (Aldrich Chemical Co.) was added. The mixture was cooled in the freezer for 1 hour and the resulting solid was collected by vacuum filtration and recrystallized from methyl alcohol to give 6-[6-(4-(2-hydroxyethyl)piperidylhexoxy)]flavone hydrochloride which was dried over P205 in high vacuum at 100° C. (yield=2.29 g, 76%): mp 204°-206° C.

Provenance & Evidence