(2s)-1-(4-Benzo[b]furanoxy)-3-(4-(3-(3-dimethylaminopropyl)-benzo[b]thiophen-2-yl)piperidin-1-yl)-2-propanol oxalate hydrate → (2S)-1-(7-Benzo[b]furanoxy)-3-(4-(3-(3-dimethylaminopropyl)-benzo[b]thiophen-2-yl)piperidin-1-yl)-2-propanol Oxalate Hemihydrate

Participants

Reaction Steps

A solution 4-(3-(3-dimethylaminopropyl)benzo[b]thiophen-2-yl)piperidine (0.075 g, 0.248 mmol, prepared in example 15) and (S)-(+)-7-(oxiranylmethoxy)benzo[b]furan (0.047 g, 0.248 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/10% methanol/1% ammonium hydroxide in dichloromethane gradient elution) to give the title compound as a yellow oil (0.039 g, 32%). The oxalate was prepared to give the title compound. FDMS m/e=493 (M++1 of free base). C29H36N2O3S.C2H2O4.0.5H2O

Provenance & Evidence