Allyl trans-2-(3-bromo-2-oxopropyl)-3-methoxy-1-piperidinecarboxylate → Allyl trans-2-[3-(7-chloro-6-(4-chlorophenoxy)-quinazolin-4(3H)-on-3-yl)-2-oxopropyl]-3-methoxypiperidine-1-carboxylate

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Reaction Steps

Under a nitrogen atmosphere in a flame-dried flask at room temperature and with magnetic stirring, 0.921 g (0.003 mol) of 7-chloro-6-(4-chlorophenoxy)quinazolin-4(3H)-one was slurried in 3.0 ml of 1.1N sodium methoxide. After 15 minutes, 1.00 g (0.003 mol) of allyl trans-2-(3-bromo-2-oxopropyl)-3-methoxy-1-piperidinecarboxylate in 10 ml of methanol was added dropwise. After 2 hours, the reaction mixture was evaporated under reduced pressure, and the residue treated with water. The aqueous solution was extracted three times with 75 ml of dichloromethane. The combined extracts were dried over anhydrous magnesium sulfate, filtered, and evaporated to afford the title compound: yield 1.28 g (76%); m.p. 138°-141° C. H-NMR(CDCl3) 1.3 to 1.9 (m, 4H), 2.6-3.4 (m, 6H), 3.3 (s, 3H), 4.9 (s, 2H), 4.5-6.2 (m, 5H), 7.1 (q, 4H), 7.6 (s, 1H), 7.8 (d, 2H) ppm.

Provenance & Evidence