Hydrochloric Acid → HCID 70228233, compound

Participants

Reaction Steps

(R)-1-[3-[[2,2-bis(4-Fluorophenyl)ethenyl]oxy]propyl]-3-piperidine carboxylic acid ethyl ester tartrate (3.8 g, 0.0065 mol) (prepared as described in Method D) was dissolved in ethanol (25 ml) and 12N sodium hydroxide solution (2.2 ml) was introduced at 5°. After stirring the solution at room temperature for 4.8 h, the pH of the reaction mixture was adjusted to ca. 7 with 4N hydrochloric acid solution, and the mixture was evaporated to a residue in vacuo. Water (25 ml) was added, and the mixture was extracted with dichloromethane (3×50 ml). The combined extracts were dried (MgSO4) and evaporated to a foam, which was dissolved in toluene (1.5 ml) and warmed to 40°. Methanol (0.27 ml) was introduced followed by chlorotrimethylsilane (0.83 ml). The product precipitated slowly, and after the suspension had been allowed to stand for 18 h at room temperature it was collected by filtration. The title compound (2.9 g, quant.) was obtained as white crystals, m.p. 177°-180° (after drying in vacuo). HPLC retention time 12.55 (gradient elution, water/35-50% acetonitrile, aqueous phase containing 0.1M ammonium sulphate solution).

Provenance & Evidence