合成路线1

Condensation of 1-benzyl-4-(3-methoxyphenyl)aminopiperidine (I) with oxalyl chloride, followed by Friedel-Crafts cyclization in the presence of AlCl3, furnished the isatin (II), which was reduced to indole (III) by means of borane-dimethyl sulfide complex. Removal of the N-benzyl protecting group of (III) to afford piperidine (IV) was achieved by treatment with chloroethyl chloroformate, followed by methanolysis of the intermediate chloroethyl carbamate. 4-Fluorophenethyl bromide (VI) was prepared from the corresponding alcohol (V) by means of the reagent generated from N-bromosuccinimide and triphenyl phosphine. Piperidine (IV) was then condensed with bromide (VI) to provide adduct (VII). Finally, the indole ring of (VII) was reduced to the required indoline using borane in THF.