Synthesis of [2H7]indatraline.
Deuterium-labelled indatraline was synthesized in high efficiency employing a Friedel-Crafts alkylation of [(2)H6]benzene with (E)-3-(3,4-dichlorophenyl)acrylic acid as a key step. The desired labelling of the final compound was ascertained in two ways, by incorporation of [(2)H6]benzene in the target molecule and additionally by deuterium transfer to the non-deuterated aryl moiety of the Friedel-Crafts alkylation product from [(2)H6]benzene, the latter thus serving as reagent and solvent.
Department of Pharmacy-Center for Drug Research, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, D-81377, München, Germany.
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D003903:Deuterium / Q000737:chemistry*; D007189:Indans / Q000138:chemical synthesis*; D008744:Methylamines / Q000138:chemical synthesis*; D019275:Radiopharmaceuticals / Q000138:chemical synthesis*
D007189:Indans; D008744:Methylamines; D019275:Radiopharmaceuticals; C418119:indatraline; D003903:Deuterium
Friedel-Crafts acylation; Friedel-Crafts alkylation; H/D exchange; Indatraline; depression; deuterium-labelled compounds; triple reuptake inhibitor