Scale-Up Synthesis of Antidepressant Drug Vilazodone

A scale-up synthesis of antidepressant drug vilazodone was accomplished in five steps. Friedel–Crafts acylation of 1-tosyl-1 H -indole-5-carbonitrile with 4-chlorobutyryl chloride, selective deoxygenation in NaBH 4 /CF 3 COOH system coupled with ethyl 5-(piperazin-1-yl)-benzofuran-2-carboxylate hydrochloride, one-step deprotection and esterolysis, and the final ammonolysis led to the target molecule vilazodone in 52.4% overall yield and 99.7% purity. This convenient and economical procedure is remarkably applicable for scale-up production.