(3S,4R)-4-(4-Fluoro­phen­yl)-3-(hydroxy­meth­yl)piperidinium chloride1

Abstract

The title compound, C12H17FNO+·Cl−, is a degradation impurity of paroxetine hydro­chloride hemihydrate (PAXIL), an anti­depressant belonging to the group of drugs called selective serotonin reuptake inhibitors (SSRIs). Similar to the paroxetine hydro­chloride salt with protonation having taken place on the basic piperidine ring, the degradation impurity also exists as the hydro­chloride salt. The cyclic six-membered piperidinium ring adopts a chair conformation with the hydroxy­methyl and 4-fluoro­phenyl groups in the equatorial positions. The ions form a tape along the b axis through charge-assisted N+—H⋯Cl− hydrogen bonds; these tapes are connected by O—H⋯Cl− hydrogen bonds along the a axis