(S)-(+)-4-(oxiranylmethoxy)benzo[b]thiophene → 4-(3-Ethylbenzo[b]thiophen-2-yl)piperidine

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A solution 4-hydroxy-4-(3-ethylbenzo[b]thiophen-2-yl)piperidine (0.069 g, 0.281 mmol) and (S)-(+)-4-(oxiranylmethoxy)-benzo[b]thiophene (0.058 g, 0.281 mmol) in methanol (3 mL) was heated at reflux for 18 hours and then cooled and evaporated. The residue was purified using silica gel chromatography (dichloromethane/1% methanol in dichloromethane) to give the free base of the final title compound as a clear colorless oil (0.050 g, 39%). The oxalate salt was prepared to give the title compound. FDMS m/e=452 (M++1 of free base). C26H29NO2S2.C2H2O4

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