132813-14-0

132812-72-7

132813-14-0

General procedure for the synthesis of 2-chloro-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine from 4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine as 4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine: 80.0 g of 4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b] Pyridin-2(1H)-one was dissolved in 520 mL of dimethylformamide and cooled to 5 °C. Under stirring, 36.84 g of phosphorus pentachloride was added in 10 portions. After addition, the temperature of the reaction system was raised to 15 °C and the reaction was continued for 3 hours. Upon completion of the reaction, 520 mL of purified water was added to the reaction mixture and stirred at 10 °C for 1 hour. The reaction solution was filtered using a Brinell funnel (Coors), the precipitated crystals were collected and the filter cake was washed with 300 mL of purified water. The resulting crystals were dried at 70 °C to afford 80.0 g of off-white 2-chloro-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine in 93.6% yield.