Piperidine → 5-Chloro-3-piperidino-2-phenyl-benzo(b)thiophene

Participants

Reaction Steps

20 g (72 mmole) of α-(4-chlorophenylthio)-phenylacetic acid and 20 milliliters (280 mmole) of SOCl2 are refluxed for 3 hours. After the excess SOCl2 has been removed, the crude acid chloride is dissolved in 100 milliliters of dioxan and, with stirring the cooling, 21.2 milliliters (290 mmole) of piperidine are added dropwise. After dilution in water, the mixture is extracted with CH2Cl2. By evaporating the organic phase dried over Na2SO4, 22.6 g (91% theory) of the piperidinium salt of α-(4-chlorophenylthio)-phenylacetic acid are obtained: colourless rods, mp 125°-126° (benzene/petroleum ether).

Provenance & Evidence