“…R f = 0.43 (20% ethyl acetate in petroleum ether); IR (neat) ν max /cm 2-Chlorophenyl(piperidin-1-yl)methanethione (1f). 62 2-Chlorobenzaldehyde (281 mg, 2.00 mmol), elemental sulfur (64.0 mg, 2.00 mmol), and piperidine (0.400 mL, 4.00 mmol) were heated at 120 °C for 4 h in the presence of a catalytic amount of p-toluene sulfonic acid (17.2 mg, 0.100 mmol). Flash column chromatography (10% ethyl acetate in petroleum ether) gave pure 1f as a yellow solid (120 mg, 0.50 mmol, 25%).…”