Improved Industrial Synthesis of Antidepressant Sertraline

( cis -1 S )-4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro- N -methyl-1-naphthalenamine hydrochloride, or sertraline hydrochloride, is a very effective antidepressant. This report presents a novel industrial synthesis of sertraline hydrochloride that is in many respects more advantageous than processes reported thus far. N -[4-(3,4-Dichlorophenyl)-3,4-dihydro-1(2 H )-naphthalenylidene]-methanamine N -oxide is used as intermediate in our process, which is a stable compound in normal conditions. It can be obtained in a simple reaction from the corresponding tetralone in good yield, using acceptable reagents with regard to environmental and safety respects. Its reduction to the desired cis -racemic amine is stereoselective, and thus it provides sertraline hydrochloride with a purity required for pharmaceutical ingredients.