N-phenylbenzenesulfonamide

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of N-phenylbenzenesulphonamide (2.34 g) in dry N,N-dimethylformamide (10 cc) is added dropwise to a suspension of sodium hydride (0.24 g, 80% suspension in oil) in N,N-dimethylformamide (50 cc). After 15 minutes' stirring, a solution of 1-(3-chloropropyl)-4-phenyl-1,2,3,6-tetrahydropyridine (2.34 g) in N,N-dimethylformamide (20 cc) is added. The reaction mixture is heated to 140° C. for 1 hour and then cooled and poured into a mixture of water (200 cc) and ethyl acetate (200 cc). The organic phase is washed with water, is dried over magnesium sulphate and is concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a column of silica gel (0.2-0.063-mm particle size, 4-cm diameter, 40-cm height) and eluted with dichloromethane and with a mixture of dichloromethane and ethanol (98-2 and 96-4 by volume), fractions 250-cc being collected. Fractions 5 to 9 are combined and concentrated to dryness under reduced pressure (2.7 kPa). After recrystallization from isopropyl ether (150 cc), N-[3-(4-phenyl-1,2,3,6-tetrahydropyridyl)propyl]-N-phenylbenzenesulphonamide (2.4 g) is obtained, melting at 112° C. cooled The organic phase is washed with water is dried over magnesium sulphate is concentrated to dryness under reduced pressure (2.7 kPa) The residue is chromatographed on a column of silica gel (0.2-0.063-mm particle size, 4-cm diameter, 40-cm height) eluted with dichloromethane and with a mixture of dichloromethane and ethanol (98-2 and 96-4 by volume), fractions 250-cc being collected concentrated to dryness under reduced pressure (2.7 kPa) After recrystallization from isopropyl ether (150 cc)

反応条件: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of N-phenylbenzenesulphonamide (2.34 g) in dry N,N-dimethylformamide (10 cc) is added dropwise to a suspension of sodium hydride (0.24 g, 80% suspension in oil) in N,N-dimethylformamide (50 cc). After 15 minutes' stirring, a solution of 1-(3-chloropropyl)-4-phenyl-1,2,3,6-tetrahydropyridine (2.34 g) in N,N-dimethylformamide (20 cc) is added. The reaction mixture is heated to 140° C. for 1 hour and then cooled and poured into a mixture of water (200 cc) and ethyl acetate (200 cc). The organic phase is washed with water, is dried over magnesium sulphate and is concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a column of silica gel (0.2-0.063-mm particle size, 4-cm diameter, 40-cm height) and eluted with dichloromethane and with a mixture of dichloromethane and ethanol (98-2 and 96-4 by volume), fractions 250-cc being collected. Fractions 5 to 9 are combined and concentrated to dryness under reduced pressure (2.7 kPa). After recrystallization from isopropyl ether (150 cc), N-[3-(4-phenyl-1,2,3,6-tetrahydropyridyl)propyl]-N-phenylbenzenesulphonamide (2.4 g) is obtained, melting at 112° C. cooled The organic phase is washed with water is dried over magnesium sulphate is concentrated to dryness under reduced pressure (2.7 kPa) The residue is chromatographed on a column of silica gel (0.2-0.063-mm particle size, 4-cm diameter, 40-cm height) eluted with dichloromethane and with a mixture of dichloromethane and ethanol (98-2 and 96-4 by volume), fractions 250-cc being collected concentrated to dryness under reduced pressure (2.7 kPa) After recrystallization from isopropyl ether (150 cc)

反応条件: temp:0.00; pressure:0.00; stir:

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: The title compound was synthesized by triturating aniline (0.5 g, 5.36 mmol), powdered sodium bicarbonate (0.9 g, 1.07 mmol) and benzene sulfonyl chloride (0.95 g, 5.36 mmol) for 10 min at rt. Then reaction mixture was stirred with water at 60° C. for 30 minutes, filtered, washed with water and dried to gave 17 (0.85 g, 68%). Product was purified by FCC by using eluent as in 15 to give 17 as white flakes (0.79 g), mp: 107-109° C. (lit33A 110° C.); IR (CHCl3) 3256, 1599, 1331, 1162, cm−1; 1H NMR (500 MHz, DMSOD6) δ 6.4 (br, 1H, NH), and 7.04-7.77 (m, 10H, aromatic). HRMS calcd 256.04027 (C12H11NO2S.Na+), found 256.04016. The title compound was synthesized Then reaction mixture filtered washed with water dried

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

実験手順: The title compound was synthesized by triturating aniline (0.5 g, 5.36 mmol), powdered sodium bicarbonate (0.9 g, 1.07 mmol) and benzene sulfonyl chloride (0.95 g, 5.36 mmol) for 10 min at rt. Then reaction mixture was stirred with water at 60° C. for 30 minutes, filtered, washed with water and dried to gave 17 (0.85 g, 68%). Product was purified by FCC by using eluent as in 15 to give 17 as white flakes (0.79 g), mp: 107-109° C. (lit33A 110° C.); IR (CHCl3) 3256, 1599, 1331, 1162, cm−1; 1H NMR (500 MHz, DMSOD6) δ 6.4 (br, 1H, NH), and 7.04-7.77 (m, 10H, aromatic). HRMS calcd 256.04027 (C12H11NO2S.Na+), found 256.04016. The title compound was synthesized Then reaction mixture filtered washed with water dried

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

実験手順: Example 2.1 was repeated, using 14.4 mg of cuprous oxide (0.1 mmoles), 117 mg of Chxn-Py-Al (0.4 mmoles), 472 mg of benzenesulphonamide (3 mmoles), 224 μl of iodobenzene (2 mmoles), 1.04 g of caesium carbonate (3.2 mmoles), 600 mg of ground and activated 3 Å molecular sieve and 1.6 ml of DMF.

反応条件: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of N-phenylbenzenesulphonamide (2.34 g) in dry N,N-dimethylformamide (10 cc) is added dropwise to a suspension of sodium hydride (0.24 g, 80% suspension in oil) in N,N-dimethylformamide (50 cc). After 15 minutes' stirring, a solution of 1-(3-chloropropyl)-4-phenyl-1,2,3,6-tetrahydropyridine (2.34 g) in N,N-dimethylformamide (20 cc) is added. The reaction mixture is heated to 140° C. for 1 hour and then cooled and poured into a mixture of water (200 cc) and ethyl acetate (200 cc). The organic phase is washed with water, is dried over magnesium sulphate and is concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a column of silica gel (0.2-0.063-mm particle size, 4-cm diameter, 40-cm height) and eluted with dichloromethane and with a mixture of dichloromethane and ethanol (98-2 and 96-4 by volume), fractions 250-cc being collected. Fractions 5 to 9 are combined and concentrated to dryness under reduced pressure (2.7 kPa). After recrystallization from isopropyl ether (150 cc), N-[3-(4-phenyl-1,2,3,6-tetrahydropyridyl)propyl]-N-phenylbenzenesulphonamide (2.4 g) is obtained, melting at 112° C. cooled The organic phase is washed with water is dried over magnesium sulphate is concentrated to dryness under reduced pressure (2.7 kPa) The residue is chromatographed on a column of silica gel (0.2-0.063-mm particle size, 4-cm diameter, 40-cm height) eluted with dichloromethane and with a mixture of dichloromethane and ethanol (98-2 and 96-4 by volume), fractions 250-cc being collected concentrated to dryness under reduced pressure (2.7 kPa) After recrystallization from isopropyl ether (150 cc)