2-(4-chlorophenyl)butanenitrile

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: rac-2-[1-(4-Chloro-phenyl)-propyl]-4,5-dihydro-1H-imidazole was prepared from rac-2-(4-chloro-phenyl)butyronitrile and ethylene diamine in analogy to Example 22: colourless powder; MS (ISP): 223.0 ((M+H)+.).

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: rac-2-[1-(4-Chloro-phenyl)-propyl]-4,5-dihydro-1H-imidazole was prepared from rac-2-(4-chloro-phenyl)butyronitrile and ethylene diamine in analogy to Example 22: colourless powder; MS (ISP): 223.0 ((M+H)+.).

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a suspension of 0.42 g (10.5 mmol) NaH (60% dispersion in mineral oil) were added at ambient temperature 1.67 g (11 mmol) 4-chlorophenyl-acetonitrile in 10 ml anhydrous tetrahydrofuran. The reaction mixture was stirred at ambient temperature for 2 hours and then cooled to −20° C. 0.78 ml (10.5 mmol) Bromoethane was added drop-wise to the reaction mixture over 30 minutes. The reaction was warmed to ambient temperature while stirring over 2 hours. The reaction mixture was quenched by addition of 20 ml of saturated ammonium chloride solution. Dichloromethane was added, the organic phase was separated and the aqueous phase washed with dichloromethane. The combined organic phase was dried over MgSO4 and evaporated to afford rac-2-(4-chloro-phenyl)butyronitrile as a brown oil that did not require further purification. NMR (CDCl3, ppm): 0.80 (3H, t), 1.82 (2H, dq), 3.64 (1H, t), 7.30-7.15 (4H, m). cooled to −20° C The reaction was warmed to ambient temperature while stirring over 2 hours The reaction mixture was quenched by addition of 20 ml of saturated ammonium chloride solution Dichloromethane was added the organic phase was separated the aqueous phase washed with dichloromethane The combined organic phase was dried over MgSO4 evaporated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a suspension of 0.42 g (10.5 mmol) NaH (60% dispersion in mineral oil) were added at ambient temperature 1.67 g (11 mmol) 4-chlorophenyl-acetonitrile in 10 ml anhydrous tetrahydrofuran. The reaction mixture was stirred at ambient temperature for 2 hours and then cooled to −20° C. 0.78 ml (10.5 mmol) Bromoethane was added drop-wise to the reaction mixture over 30 minutes. The reaction was warmed to ambient temperature while stirring over 2 hours. The reaction mixture was quenched by addition of 20 ml of saturated ammonium chloride solution. Dichloromethane was added, the organic phase was separated and the aqueous phase washed with dichloromethane. The combined organic phase was dried over MgSO4 and evaporated to afford rac-2-(4-chloro-phenyl)butyronitrile as a brown oil that did not require further purification. NMR (CDCl3, ppm): 0.80 (3H, t), 1.82 (2H, dq), 3.64 (1H, t), 7.30-7.15 (4H, m). cooled to −20° C The reaction was warmed to ambient temperature while stirring over 2 hours The reaction mixture was quenched by addition of 20 ml of saturated ammonium chloride solution Dichloromethane was added the organic phase was separated the aqueous phase washed with dichloromethane The combined organic phase was dried over MgSO4 evaporated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: rac-2-[1-(4-Chloro-phenyl)-propyl]-4,5-dihydro-1H-imidazole was prepared from rac-2-(4-chloro-phenyl)butyronitrile and ethylene diamine in analogy to Example 22: colourless powder; MS (ISP): 223.0 ((M+H)+.).

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a suspension of 0.42 g (10.5 mmol) NaH (60% dispersion in mineral oil) were added at ambient temperature 1.67 g (11 mmol) 4-chlorophenyl-acetonitrile in 10 ml anhydrous tetrahydrofuran. The reaction mixture was stirred at ambient temperature for 2 hours and then cooled to −20° C. 0.78 ml (10.5 mmol) Bromoethane was added drop-wise to the reaction mixture over 30 minutes. The reaction was warmed to ambient temperature while stirring over 2 hours. The reaction mixture was quenched by addition of 20 ml of saturated ammonium chloride solution. Dichloromethane was added, the organic phase was separated and the aqueous phase washed with dichloromethane. The combined organic phase was dried over MgSO4 and evaporated to afford rac-2-(4-chloro-phenyl)butyronitrile as a brown oil that did not require further purification. NMR (CDCl3, ppm): 0.80 (3H, t), 1.82 (2H, dq), 3.64 (1H, t), 7.30-7.15 (4H, m). cooled to −20° C The reaction was warmed to ambient temperature while stirring over 2 hours The reaction mixture was quenched by addition of 20 ml of saturated ammonium chloride solution Dichloromethane was added the organic phase was separated the aqueous phase washed with dichloromethane The combined organic phase was dried over MgSO4 evaporated

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 2-(4-chlorophenyl)butanenitrile (6.2 g, 35 mmol) in 50 mL DMF stirred at 0° C., was treated with NaH (0.99 g, 41 mmol). The mixture was stirred at 0° C. for 30 minutes, and was treated with MeI (7.3 g, 52 mmol). The mixture was stirred at 0° C. to room temperature for 2 hours, and was carefully quenched with H2O, and neutralized with 10% HCl to pH=5. The mixture was extracted with ether (3×50 mL). The combined organic layers were washed with brine (30 mL), dried over anhydrous Na2SO4, concentrated in vacuo, and purified by column chromatography eluting with 10% EtOAc/hexane to give 6.5 g of the product as a pale yellow oil. The mixture was stirred at 0° C. for 30 minutes The mixture was stirred at 0° C. to room temperature for 2 hours was carefully quenched with H2O The mixture was extracted with ether (3×50 mL) The combined organic layers were washed with brine (30 mL) dried over anhydrous Na2SO4 concentrated in vacuo purified by column chromatography eluting with 10% EtOAc/hexane

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of NaH (4.0 g, 99 mmol) in 50 mL NMP stirred at 0° C., was treated dropwise with a mixture of bromoethane (11 g, 99 mmol) and 2-(4-chlorophenyl)acetonitrile (15 g, 99 mmol) in 20 mL ether. The mixture was stirred at room temperature for 2 hours, cooled to 0° C., and quenched carefully with H2O. The resulting mixture was neutralized with 10% HCl to a pH of 5. The mixture was extracted with ether (3×50 mL). The combined organic layers were washed with brine (30 mL), dried over anhydrous Na2SO4, concentrated in vacuo, and purified by column chromatography eluting with 5% EtOAc/hexane to give 9.1 g of the product as a pale yellow oil. The mixture was stirred at room temperature for 2 hours cooled to 0° C. quenched carefully with H2O The mixture was extracted with ether (3×50 mL) The combined organic layers were washed with brine (30 mL) dried over anhydrous Na2SO4 concentrated in vacuo purified by column chromatography eluting with 5% EtOAc/hexane

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 2-(4-chlorophenyl)butanenitrile (6.2 g, 35 mmol) in 50 mL DMF stirred at 0° C., was treated with NaH (0.99 g, 41 mmol). The mixture was stirred at 0° C. for 30 minutes, and was treated with MeI (7.3 g, 52 mmol). The mixture was stirred at 0° C. to room temperature for 2 hours, and was carefully quenched with H2O, and neutralized with 10% HCl to pH=5. The mixture was extracted with ether (3×50 mL). The combined organic layers were washed with brine (30 mL), dried over anhydrous Na2SO4, concentrated in vacuo, and purified by column chromatography eluting with 10% EtOAc/hexane to give 6.5 g of the product as a pale yellow oil. The mixture was stirred at 0° C. for 30 minutes The mixture was stirred at 0° C. to room temperature for 2 hours was carefully quenched with H2O The mixture was extracted with ether (3×50 mL) The combined organic layers were washed with brine (30 mL) dried over anhydrous Na2SO4 concentrated in vacuo purified by column chromatography eluting with 10% EtOAc/hexane

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of NaH (4.0 g, 99 mmol) in 50 mL NMP stirred at 0° C., was treated dropwise with a mixture of bromoethane (11 g, 99 mmol) and 2-(4-chlorophenyl)acetonitrile (15 g, 99 mmol) in 20 mL ether. The mixture was stirred at room temperature for 2 hours, cooled to 0° C., and quenched carefully with H2O. The resulting mixture was neutralized with 10% HCl to a pH of 5. The mixture was extracted with ether (3×50 mL). The combined organic layers were washed with brine (30 mL), dried over anhydrous Na2SO4, concentrated in vacuo, and purified by column chromatography eluting with 5% EtOAc/hexane to give 9.1 g of the product as a pale yellow oil. The mixture was stirred at room temperature for 2 hours cooled to 0° C. quenched carefully with H2O The mixture was extracted with ether (3×50 mL) The combined organic layers were washed with brine (30 mL) dried over anhydrous Na2SO4 concentrated in vacuo purified by column chromatography eluting with 5% EtOAc/hexane