4-fluoro-N-(2-methylpropyl)benzenesulfonamide

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A microwave vial was charged with 4-fluoro-N-isobutyl-benzenesulfonamide (1.0 g, 4.32 mmol), piperazine (1.86 g, 21.60 mmol) and water (20 mL) and heated at 150° C. for 1 hour using a microwave reactor. The solid from the reaction mixture was collected by filtration, washed with water and dried to give N-isobutyl-4-piperazin-1-yl-benzenesulfonamide (1.15 g, 90%). 1H NMR (300 MHz, CDCl3) δ 7.70 (d, J=9.0 Hz, 2H), 6.90 (d, J=9.0 Hz, 2H), 4.33 (t, J=6.5 Hz, 1H), 3.32-3.25 (m, 4H), 3.05-2.99 (m, 4H), 2.73 (t, J=6.6 Hz, 2H), 1.78-1.65 (m, 1H), 0.87 (d, J=6.7 Hz, 7H). LCMS (m/z, Method A) ES+ 298.2 [M+1]+. The solid from the reaction mixture was collected by filtration washed with water dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of isobutylamine (6.64 mL, 66.8 mmol) and pyridine (6.24 mL, 77.1 mmol) in DCM (100 mL) was treated with 4-fluorobenzene sulfonyl chloride (10.0 g, 51.4 mmol) and stirred at room temperature for 18 hours. The mixture was diluted with DCM, washed with 1 N aqueous HCl, saturated aqueous NaHCO3, water and brine, dried over Na2SO4 and concentrated under vacuum. Trituration with pentane gave 4-fluoro-N-isobutyl-benzenesulfonamide (10.48 g, 88%) as a pale yellow solid. 1H NMR (400 MHz, DMSO) δ 7.88-7.81 (m, 2H), 7.63 (t, J=6.1 Hz, 1H), 7.47-7.39 (m, 2H), 2.54 (t, J=6.5 Hz, 2H), 1.67-1.55 (m, 1H), 0.80 (d, J=6.7 Hz, 6H). LCMS (m/z, Method B) ES+ 232.0 [M+1]+. washed with 1 N aqueous HCl, saturated aqueous NaHCO3, water and brine dried over Na2SO4 concentrated under vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of isobutylamine (6.64 mL, 66.8 mmol) and pyridine (6.24 mL, 77.1 mmol) in DCM (100 mL) was treated with 4-fluorobenzene sulfonyl chloride (10.0 g, 51.4 mmol) and stirred at room temperature for 18 hours. The mixture was diluted with DCM, washed with 1 N aqueous HCl, saturated aqueous NaHCO3, water and brine, dried over Na2SO4 and concentrated under vacuum. Trituration with pentane gave 4-fluoro-N-isobutyl-benzenesulfonamide (10.48 g, 88%) as a pale yellow solid. 1H NMR (400 MHz, DMSO) δ 7.88-7.81 (m, 2H), 7.63 (t, J=6.1 Hz, 1H), 7.47-7.39 (m, 2H), 2.54 (t, J=6.5 Hz, 2H), 1.67-1.55 (m, 1H), 0.80 (d, J=6.7 Hz, 6H). LCMS (m/z, Method B) ES+ 232.0 [M+1]+. washed with 1 N aqueous HCl, saturated aqueous NaHCO3, water and brine dried over Na2SO4 concentrated under vacuum

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A microwave vial was charged with 4-fluoro-N-isobutyl-benzenesulfonamide (1.0 g, 4.32 mmol), piperazine (1.86 g, 21.60 mmol) and water (20 mL) and heated at 150° C. for 1 hour using a microwave reactor. The solid from the reaction mixture was collected by filtration, washed with water and dried to give N-isobutyl-4-piperazin-1-yl-benzenesulfonamide (1.15 g, 90%). 1H NMR (300 MHz, CDCl3) δ 7.70 (d, J=9.0 Hz, 2H), 6.90 (d, J=9.0 Hz, 2H), 4.33 (t, J=6.5 Hz, 1H), 3.32-3.25 (m, 4H), 3.05-2.99 (m, 4H), 2.73 (t, J=6.6 Hz, 2H), 1.78-1.65 (m, 1H), 0.87 (d, J=6.7 Hz, 7H). LCMS (m/z, Method A) ES+ 298.2 [M+1]+. The solid from the reaction mixture was collected by filtration washed with water dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of isobutylamine (6.64 mL, 66.8 mmol) and pyridine (6.24 mL, 77.1 mmol) in DCM (100 mL) was treated with 4-fluorobenzene sulfonyl chloride (10.0 g, 51.4 mmol) and stirred at room temperature for 18 hours. The mixture was diluted with DCM, washed with 1 N aqueous HCl, saturated aqueous NaHCO3, water and brine, dried over Na2SO4 and concentrated under vacuum. Trituration with pentane gave 4-fluoro-N-isobutyl-benzenesulfonamide (10.48 g, 88%) as a pale yellow solid. 1H NMR (400 MHz, DMSO) δ 7.88-7.81 (m, 2H), 7.63 (t, J=6.1 Hz, 1H), 7.47-7.39 (m, 2H), 2.54 (t, J=6.5 Hz, 2H), 1.67-1.55 (m, 1H), 0.80 (d, J=6.7 Hz, 6H). LCMS (m/z, Method B) ES+ 232.0 [M+1]+. washed with 1 N aqueous HCl, saturated aqueous NaHCO3, water and brine dried over Na2SO4 concentrated under vacuum