3-chloro-N,N-diphenylpropanamide

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: A mixture of 12.0 g (0.040 mole) of α,α-bis(4-fluorophenyl)-4-piperidine methanol, 10.3 g (0.040 mole) of 3-chloro-N,N-diphenylpropanamide, 17.0 g (0.160 mole) of anhydrous sodium carbonate and 0.3 g (0.002 mole) of potassium iodide in 100 ml of N,N-dimethylformamide was heated on a steam bath for 16 h. The mixture was poured into 2 L of water and a solid precipitated. After standing 3 h, the solid was collected by filtration, washed with water, dried and recrystallized from benzene-petroleum ether (30°-60° C.) to yield 18.7 g (90%) of a white solid, mp 160°-162° C. was heated on a steam bath for 16 h a solid precipitated the solid was collected by filtration washed with water dried recrystallized from benzene-petroleum ether (30°-60° C.)

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

実験手順: To a solution of 40.6 g (0.240 mole) of diphenylamine in 150 ml of tetrahydrofuran (THF) was added dropwise a solution of 20.0 g (0.160 mole) of 3-chloropropionyl chloride in 100 ml of THF. The reaction mixture was stirred mechanically and the temperature maintained between 5° and 15° C. throughout the addition. After the final addition, the solution was filtered to remove solid precipitates, and the filtrate was concentrated under reduced pressure. The residue was partitioned between methylene chloride and water (200 ml each). The methylene chloride layer was washed with water and brine, dried (MgSO4) and concentrated under reduced pressure to give an amorphous solid. The solid was recrystallized from THF to yield 20.0 g (48%) of the title compound as a white, crystalline solid, mp 93°-94° C. the temperature maintained between 5° and 15° C. throughout the addition After the final addition the solution was filtered to remove solid precipitates the filtrate was concentrated under reduced pressure The residue was partitioned between methylene chloride and water (200 ml each) The methylene chloride layer was washed with water and brine dried (MgSO4) concentrated under reduced pressure to give an amorphous solid The solid was recrystallized from THF

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

実験手順: A mixture of 12.0 g (0.040 mole) of α,α-bis(4-fluorophenyl)-4-piperidine methanol, 10.3 g (0.040 mole) of 3-chloro-N,N-diphenylpropanamide, 17.0 g (0.160 mole) of anhydrous sodium carbonate and 0.3 g (0.002 mole) of potassium iodide in 100 ml of N,N-dimethylformamide was heated on a steam bath for 16 h. The mixture was poured into 2 L of water and a solid precipitated. After standing 3 h, the solid was collected by filtration, washed with water, dried and recrystallized from benzene-petroleum ether (30°-60° C.) to yield 18.7 g (90%) of a white solid, mp 160°-162° C. was heated on a steam bath for 16 h a solid precipitated the solid was collected by filtration washed with water dried recrystallized from benzene-petroleum ether (30°-60° C.)

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

実験手順: A mixture of 12.0 g (0.040 mole) of α,α-bis(4-fluorophenyl)-4-piperidine methanol, 10.3 g (0.040 mole) of 3-chloro-N,N-diphenylpropanamide, 17.0 g (0.160 mole) of anhydrous sodium carbonate and 0.3 g (0.002 mole) of potassium iodide in 100 ml of N,N-dimethylformamide was heated on a steam bath for 16 h. The mixture was poured into 2 L of water and a solid precipitated. After standing 3 h, the solid was collected by filtration, washed with water, dried and recrystallized from benzene-petroleum ether (30°-60° C.) to yield 18.7 g (90%) of a white solid, mp 160°-162° C. was heated on a steam bath for 16 h a solid precipitated the solid was collected by filtration washed with water dried recrystallized from benzene-petroleum ether (30°-60° C.)

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

実験手順: To a solution of 40.6 g (0.240 mole) of diphenylamine in 150 ml of tetrahydrofuran (THF) was added dropwise a solution of 20.0 g (0.160 mole) of 3-chloropropionyl chloride in 100 ml of THF. The reaction mixture was stirred mechanically and the temperature maintained between 5° and 15° C. throughout the addition. After the final addition, the solution was filtered to remove solid precipitates, and the filtrate was concentrated under reduced pressure. The residue was partitioned between methylene chloride and water (200 ml each). The methylene chloride layer was washed with water and brine, dried (MgSO4) and concentrated under reduced pressure to give an amorphous solid. The solid was recrystallized from THF to yield 20.0 g (48%) of the title compound as a white, crystalline solid, mp 93°-94° C. the temperature maintained between 5° and 15° C. throughout the addition After the final addition the solution was filtered to remove solid precipitates the filtrate was concentrated under reduced pressure The residue was partitioned between methylene chloride and water (200 ml each) The methylene chloride layer was washed with water and brine dried (MgSO4) concentrated under reduced pressure to give an amorphous solid The solid was recrystallized from THF

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: A mixture of 12.0 g (0.040 mole) of α,α-bis(4-fluorophenyl)-4-piperidine methanol, 10.3 g (0.040 mole) of 3-chloro-N,N-diphenylpropanamide, 17.0 g (0.160 mole) of anhydrous sodium carbonate and 0.3 g (0.002 mole) of potassium iodide in 100 ml of N,N-dimethylformamide was heated on a steam bath for 16 h. The mixture was poured into 2 L of water and a solid precipitated. After standing 3 h, the solid was collected by filtration, washed with water, dried and recrystallized from benzene-petroleum ether (30°-60° C.) to yield 18.7 g (90%) of a white solid, mp 160°-162° C. was heated on a steam bath for 16 h a solid precipitated the solid was collected by filtration washed with water dried recrystallized from benzene-petroleum ether (30°-60° C.)

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

実験手順: To a solution of 40.6 g (0.240 mole) of diphenylamine in 150 ml of tetrahydrofuran (THF) was added dropwise a solution of 20.0 g (0.160 mole) of 3-chloropropionyl chloride in 100 ml of THF. The reaction mixture was stirred mechanically and the temperature maintained between 5° and 15° C. throughout the addition. After the final addition, the solution was filtered to remove solid precipitates, and the filtrate was concentrated under reduced pressure. The residue was partitioned between methylene chloride and water (200 ml each). The methylene chloride layer was washed with water and brine, dried (MgSO4) and concentrated under reduced pressure to give an amorphous solid. The solid was recrystallized from THF to yield 20.0 g (48%) of the title compound as a white, crystalline solid, mp 93°-94° C. the temperature maintained between 5° and 15° C. throughout the addition After the final addition the solution was filtered to remove solid precipitates the filtrate was concentrated under reduced pressure The residue was partitioned between methylene chloride and water (200 ml each) The methylene chloride layer was washed with water and brine dried (MgSO4) concentrated under reduced pressure to give an amorphous solid The solid was recrystallized from THF