Sodium Iodide → 6-[6-(4-hydroxypiperidinyl)hexoxy]-3-methoxy-4H-1-benzopyran-4-one

Participants

Reaction Steps

A mixture of 2 g of 6-(6-chlorohexoxy)-3-methoxy-4H-1-benzopyran-4-one, 1 g of sodium iodide, 0.6 g of potassium carbonate, and 1.4 g of 4-hydroxypiperidine was refluxed in butanone for 96 hours. The solvent was removed and the residue stirred with ethyl acetate and filtered. The solution was washed with water and then dried over sodium sulfate. The solvent was removed to give an oil which was chromatographed over silica gel to give 2 g of 6-[6-(4-hydroxypiperidinyl)hexoxy]-3-methoxy-4H-1-benzopyran-4-one which was converted to the hydrochloride salt by dissolving in ethyl acetate and adding 1N ethereal HCL: mp 124°-125° C.

Provenance & Evidence