Pipecolic Acid → HCID 13281222, compound

Participants

Reaction Conditions

Reaction Steps

4-Bromo-2-fluoro-5-hydroxyphenyl isocyanate (3 g) was dissolved in chlorobenzene (5 ml), and a solution of pipecolic acid (1.7 g) and sodium hydroxide (0.56 g) in water (5 ml) was added thereto, followed by stirring at room temperature (ca. 20° C.) overnight. The aqueous layer was washed with ether, made acidic with an aqueous hydrochloric acid solution and heated under reflux for 2 hours. After allowed to cool, the resulting mixture was extracted with methylene chloride (300 ml). The extract was washed with sodium bicarbonate solution, dried and concentrated. The residue was recrystallized from ether to give 1.75 g of 2-(4-bromo-2-fluoro-5-hydroxyphenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine-1,3(2H,8aH)-dione. M.P., 196°-199° C.

Provenance & Evidence