title: Structure elucidation of a process-related impurity of dapoxetine.
abstract: Unknown by-product associated with the synthesis of dapoxetine was isolated. The structure elucidation of this new compound using accurate mass data and NMR spectroscopy is presented herein. The unambiguous resonance assignment concluded to the formation of a tricyclic compound 4-phenyl-2H,3H,4H-naphtho[1,2-b]pyran, a new impurity of dapoxetine which has never been reported previously. A proposed mechanism for the formation of the new carbon-carbon bond is discussed. For the separation of dapoxetine and the process-related impurities, a gradient HPLC method was developed.
authors.affiliation: Department of Pharmaceutical Chemistry, Semmelweis University, Hőgyes Endre Street 9, H-1092 Budapest, Hungary.
authors.forename: András
authors.initials: A
authors.lastname: Darcsi
authors.affiliation: Department of Pharmaceutical Chemistry, Semmelweis University, Hőgyes Endre Street 9, H-1092 Budapest, Hungary.
authors.forename: Gergő
authors.initials: G
authors.lastname: Tóth
authors.affiliation: Department of Pharmaceutical Chemistry, Semmelweis University, Hőgyes Endre Street 9, H-1092 Budapest, Hungary.
authors.forename: József
authors.initials: J
authors.lastname: Kökösi
authors.affiliation: Department of Pharmaceutical Chemistry, Semmelweis University, Hőgyes Endre Street 9, H-1092 Budapest, Hungary. Electronic address: beni.szabolcs@pharma.semmelweis-univ.hu.
authors.forename: Szabolcs
authors.initials: S
authors.lastname: Béni
mesh_terms: D001578:Benzopyrans / Q000737:chemistry / Q000302:isolation & purification; D001596:Benzylamines / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D004340:Drug Contamination; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D009281:Naphthalenes / Q000737:chemistry*; D017367:Selective Serotonin Reuptake Inhibitors / Q000737:chemistry*
chemical_list: D001578:Benzopyrans; D001596:Benzylamines; D009281:Naphthalenes; D017367:Selective Serotonin Reuptake Inhibitors; C080598:dapoxetine
keywords: HPLC–DAD; Impurity profiling; NMR; Priligy; Ring closure mechanism