合成路线1

6-Fluoro-8-hydroxychroman-4-one (I) was converted to ethylene ketal (II) upon treatment with ethylene glycol and triethyl orthoformate, and subsequently alkylated with 1,2-dibromoethane under phase-transfer conditions to afford the bromoethyl ether (III). Wittig condensation of piperonal (V) with the (3-phthalimidopropyl)phosphonium salt (IV) in the presence of NaOMe in dioxan provided olefin (VI), which was hydrogenated over Pd/C to furnish the arylbutyl phthalimide (VII). Further deprotection of the phthalimido group of (VII) with CH3NH2 gave amine (VIII). Then, alkylation of (VIII) with bromide (III), followed by acid hydrolysis of the ketal function yielded the title compound.