N-[1-(4-bromophenyl)ethyl]ethanesulfonamide

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: N-(1-(4-Bromophenyl)ethyl)-N-ethylsulfonylamine (1.25 g, 4.28 mmol), and (0.75 g, 4.6 mmol) of 3-picolyl chloride hydrochloride, and (5.1 g, 37 mmol) of potassium carbonate were dissolved in 40 ml DMF. Additional 3-picolyl chloride hydrochloride (0.75 g, 4.6 mmol) was added after 30 minutes and the mixture stirred 20 h at room temperature. The mixture was diluted with 120 ml ethyl acetate and 60 ml of water and transferred to a separatory funnel. The organic layer was separated and washed twice with water. The organic layer was again separated and dried over sodium sulfate, filtered, and concentrated in vacuo to afford a dark oil. The oil was purified by radial chromatography on a 6 micron silica plate eluting with 1 to 4% methanol/dichloromethane to afford after concentration of fractions the title compound. MS calcd. 383.2; MS (M+1) 384.1. transferred to a separatory funnel The organic layer was separated washed twice with water The organic layer was again separated dried over sodium sulfate filtered concentrated in vacuo to afford a dark oil The oil was purified by radial chromatography on a 6 micron silica plate eluting with 1 to 4% methanol/dichloromethane

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

Procedure: 4-Bromo-α-methylbenzylamine (8.15 g, 40.73 mmol) and (4.15 g, 41.00 mmol) triethylamine dissolved in 150 ml dichloromethane was treated slowly with ethanesulfonyl chloride (5.27 g, 41.00 mmol) and stirred for 15 minutes. The reaction mixture was extracted with 50 ml 1N HCl/15 ml brine. The organic layer was separated, dried sodium sulfate, filtered, and concentrated in vacuo to afford the title compound. 1H NMR: 7.52 (d,2H,J=12 Hz), 7.25 (d,2H,J=12 Hz), 4.77 (m,1H), 4.63 (m,1H), 2.77 (m,2H), 1.56 (d,3H,J=8 Hz), 1.27 (t,3H,J=8 Hz). MS calcd. 292.2; MS (M+−1) 291.1. The reaction mixture was extracted with 50 ml 1N HCl/15 ml brine The organic layer was separated dried sodium sulfate, filtered concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: N-(1-(4-Bromophenyl)ethyl)-N-ethylsulfonylamine (1.25 g, 4.28 mmol), and (0.75 g, 4.6 mmol) of 3-picolyl chloride hydrochloride, and (5.1 g, 37 mmol) of potassium carbonate were dissolved in 40 ml DMF. Additional 3-picolyl chloride hydrochloride (0.75 g, 4.6 mmol) was added after 30 minutes and the mixture stirred 20 h at room temperature. The mixture was diluted with 120 ml ethyl acetate and 60 ml of water and transferred to a separatory funnel. The organic layer was separated and washed twice with water. The organic layer was again separated and dried over sodium sulfate, filtered, and concentrated in vacuo to afford a dark oil. The oil was purified by radial chromatography on a 6 micron silica plate eluting with 1 to 4% methanol/dichloromethane to afford after concentration of fractions the title compound. MS calcd. 383.2; MS (M+1) 384.1. transferred to a separatory funnel The organic layer was separated washed twice with water The organic layer was again separated dried over sodium sulfate filtered concentrated in vacuo to afford a dark oil The oil was purified by radial chromatography on a 6 micron silica plate eluting with 1 to 4% methanol/dichloromethane

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

Procedure: 4-Bromo-α-methylbenzylamine (8.15 g, 40.73 mmol) and (4.15 g, 41.00 mmol) triethylamine dissolved in 150 ml dichloromethane was treated slowly with ethanesulfonyl chloride (5.27 g, 41.00 mmol) and stirred for 15 minutes. The reaction mixture was extracted with 50 ml 1N HCl/15 ml brine. The organic layer was separated, dried sodium sulfate, filtered, and concentrated in vacuo to afford the title compound. 1H NMR: 7.52 (d,2H,J=12 Hz), 7.25 (d,2H,J=12 Hz), 4.77 (m,1H), 4.63 (m,1H), 2.77 (m,2H), 1.56 (d,3H,J=8 Hz), 1.27 (t,3H,J=8 Hz). MS calcd. 292.2; MS (M+−1) 291.1. The reaction mixture was extracted with 50 ml 1N HCl/15 ml brine The organic layer was separated dried sodium sulfate, filtered concentrated in vacuo

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

Procedure: 4-Bromo-α-methylbenzylamine (8.15 g, 40.73 mmol) and (4.15 g, 41.00 mmol) triethylamine dissolved in 150 ml dichloromethane was treated slowly with ethanesulfonyl chloride (5.27 g, 41.00 mmol) and stirred for 15 minutes. The reaction mixture was extracted with 50 ml 1N HCl/15 ml brine. The organic layer was separated, dried sodium sulfate, filtered, and concentrated in vacuo to afford the title compound. 1H NMR: 7.52 (d,2H,J=12 Hz), 7.25 (d,2H,J=12 Hz), 4.77 (m,1H), 4.63 (m,1H), 2.77 (m,2H), 1.56 (d,3H,J=8 Hz), 1.27 (t,3H,J=8 Hz). MS calcd. 292.2; MS (M+−1) 291.1. The reaction mixture was extracted with 50 ml 1N HCl/15 ml brine The organic layer was separated dried sodium sulfate, filtered concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: N-(1-(4-Bromophenyl)ethyl)-N-ethylsulfonylamine (1.25 g, 4.28 mmol), and (0.75 g, 4.6 mmol) of 3-picolyl chloride hydrochloride, and (5.1 g, 37 mmol) of potassium carbonate were dissolved in 40 ml DMF. Additional 3-picolyl chloride hydrochloride (0.75 g, 4.6 mmol) was added after 30 minutes and the mixture stirred 20 h at room temperature. The mixture was diluted with 120 ml ethyl acetate and 60 ml of water and transferred to a separatory funnel. The organic layer was separated and washed twice with water. The organic layer was again separated and dried over sodium sulfate, filtered, and concentrated in vacuo to afford a dark oil. The oil was purified by radial chromatography on a 6 micron silica plate eluting with 1 to 4% methanol/dichloromethane to afford after concentration of fractions the title compound. MS calcd. 383.2; MS (M+1) 384.1. transferred to a separatory funnel The organic layer was separated washed twice with water The organic layer was again separated dried over sodium sulfate filtered concentrated in vacuo to afford a dark oil The oil was purified by radial chromatography on a 6 micron silica plate eluting with 1 to 4% methanol/dichloromethane

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

Procedure: 4-Bromo-α-methylbenzylamine (8.15 g, 40.73 mmol) and (4.15 g, 41.00 mmol) triethylamine dissolved in 150 ml dichloromethane was treated slowly with ethanesulfonyl chloride (5.27 g, 41.00 mmol) and stirred for 15 minutes. The reaction mixture was extracted with 50 ml 1N HCl/15 ml brine. The organic layer was separated, dried sodium sulfate, filtered, and concentrated in vacuo to afford the title compound. 1H NMR: 7.52 (d,2H,J=12 Hz), 7.25 (d,2H,J=12 Hz), 4.77 (m,1H), 4.63 (m,1H), 2.77 (m,2H), 1.56 (d,3H,J=8 Hz), 1.27 (t,3H,J=8 Hz). MS calcd. 292.2; MS (M+−1) 291.1. The reaction mixture was extracted with 50 ml 1N HCl/15 ml brine The organic layer was separated dried sodium sulfate, filtered concentrated in vacuo