2-[(propan-2-ylamino)methyl]aniline

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: To a 500 ml 3-necked round bottom flask equipped with reflux condenser, thermometer, magnetic stirrer bar and nitrogen bubbler was charged 2-amino-N-(1-methylethyl)-benzylamine (148.0 g, 0.907 mol), sulfamide (87.9 g, 0.907 mol) and pyridine (975 ml) and the stirred solution heated at reflux for 5 hours under nitrogen (reaction followed by GC and HPLC). The reaction mixture allowed to cool, then pyridine removed under reduced pressure. The residue was dissolved in 5N hydrochloric acid (1000 ml) and ethyl acetate (1000 ml) and the acidic layer was extracted with further ethyl acetate (5×1000 ml). The combined organic layer was washed with 5N hydrochloric acid (250 ml), then extracted with 2N sodium hydroxide (3×1000 ml), the combined aqueous layer washed with diethyl ether (2×500 ml). Ice was then added to the aqueous layer, followed by addition of 5N hydrochloric acid with cooling and stirring of the suspension to pH 1. The oily suspension was stirred at room temperature overnight, the solid filtered and dried at room temperature under vacuum to leave an off-white solid, 3,4-dihydro-3-(1-methylethyl)-1H-2,1,3-benzothiadiazine-2,2-dioxide. To a 500 ml 3-necked round bottom flask equipped with reflux condenser the stirred solution heated at reflux for 5 hours under nitrogen (reaction followed by GC and HPLC) to cool pyridine removed under reduced pressure The residue was dissolved in 5N hydrochloric acid (1000 ml) ethyl acetate (1000 ml) and the acidic layer was extracted with further ethyl acetate (5×1000 ml) The combined organic layer was washed with 5N hydrochloric acid (250 ml) extracted with 2N sodium hydroxide (3×1000 ml) the combined aqueous layer washed with diethyl ether (2×500 ml) Ice was then added to the aqueous layer followed by addition of 5N hydrochloric acid with cooling The oily suspension was stirred at room temperature overnight the solid filtered dried at room temperature under vacuum

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

実験手順: To a 500 ml 3-necked round bottom flask equipped with reflux condenser, thermometer, magnetic stirrer bar and nitrogen bubbler was charged 2-amino-N-(1-methylethyl)-benzylamine (148.0 g, 0.907 mol), sulfamide (87.9 g, 0.907 mol) and pyridine (975 ml) and the stirred solution heated at reflux for 5 hours under nitrogen (reaction followed by GC and HPLC). The reaction mixture allowed to cool, then pyridine removed under reduced pressure. The residue was dissolved in 5N hydrochloric acid (1000 ml) and ethyl acetate (1000 ml) and the acidic layer was extracted with further ethyl acetate (5×1000 ml). The combined organic layer was washed with 5N hydrochloric acid (250 ml), then extracted with 2N sodium hydroxide (3×1000 ml), the combined aqueous layer washed with diethyl ether (2×500 ml). Ice was then added to the aqueous layer, followed by addition of 5N hydrochloric acid with cooling and stirring of the suspension to pH 1. The oily suspension was stirred at room temperature overnight, the solid filtered and dried at room temperature under vacuum to leave an off-white solid, 3,4-dihydro-3-(1-methylethyl)-1H-2,1,3-benzothiadiazine-2,2-dioxide. To a 500 ml 3-necked round bottom flask equipped with reflux condenser the stirred solution heated at reflux for 5 hours under nitrogen (reaction followed by GC and HPLC) to cool pyridine removed under reduced pressure The residue was dissolved in 5N hydrochloric acid (1000 ml) ethyl acetate (1000 ml) and the acidic layer was extracted with further ethyl acetate (5×1000 ml) The combined organic layer was washed with 5N hydrochloric acid (250 ml) extracted with 2N sodium hydroxide (3×1000 ml) the combined aqueous layer washed with diethyl ether (2×500 ml) Ice was then added to the aqueous layer followed by addition of 5N hydrochloric acid with cooling The oily suspension was stirred at room temperature overnight the solid filtered dried at room temperature under vacuum

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

実験手順: To a 500 ml 3-necked round bottom flask equipped with overhead mechanical stirrer, thermometer and nitrogen bubbler was charged 2-nitrobenzaldehyde (200 g, 1.32 mol) in methanol (1300 ml), to which was added isopropylamine (78.0 g, 113 ml, 1.32 mol) in one portion with stirring under nitrogen. The reaction mixture was then stirred for 100 minutes (followed reaction by GC), then added to a 4 litre stainless steel Parr hydrogenator, containing a suspension of 5% palladium on charcoal (13.24 g, 6% cat. loading) in methanol (500 ml) and the suspension hydrogenated under hydrogen at 60 psi for 3 hours. The suspension was filtered through a pad of celite, the pad washed with methanol (500 ml) and the combined filtrate evaporated under reduced pressure to leave a yellow oil, 2-amino-N-(1-methylethyl)-benzylamine. To a 500 ml 3-necked round bottom flask equipped with overhead mechanical stirrer The reaction mixture was then stirred for 100 minutes (followed reaction by GC) containing The suspension was filtered through a pad of celite the pad washed with methanol (500 ml) the combined filtrate evaporated under reduced pressure

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: To a 500 ml 3-necked round bottom flask equipped with reflux condenser, thermometer, magnetic stirrer bar and nitrogen bubbler was charged 2-amino-N-(1-methylethyl)-benzylamine (148.0 g, 0.907 mol), sulfamide (87.9 g, 0.907 mol) and pyridine (975 ml) and the stirred solution heated at reflux for 5 hours under nitrogen (reaction followed by GC and HPLC). The reaction mixture allowed to cool, then pyridine removed under reduced pressure. The residue was dissolved in 5N hydrochloric acid (1000 ml) and ethyl acetate (1000 ml) and the acidic layer was extracted with further ethyl acetate (5×1000 ml). The combined organic layer was washed with 5N hydrochloric acid (250 ml), then extracted with 2N sodium hydroxide (3×1000 ml), the combined aqueous layer washed with diethyl ether (2×500 ml). Ice was then added to the aqueous layer, followed by addition of 5N hydrochloric acid with cooling and stirring of the suspension to pH 1. The oily suspension was stirred at room temperature overnight, the solid filtered and dried at room temperature under vacuum to leave an off-white solid, 3,4-dihydro-3-(1-methylethyl)-1H-2,1,3-benzothiadiazine-2,2-dioxide. To a 500 ml 3-necked round bottom flask equipped with reflux condenser the stirred solution heated at reflux for 5 hours under nitrogen (reaction followed by GC and HPLC) to cool pyridine removed under reduced pressure The residue was dissolved in 5N hydrochloric acid (1000 ml) ethyl acetate (1000 ml) and the acidic layer was extracted with further ethyl acetate (5×1000 ml) The combined organic layer was washed with 5N hydrochloric acid (250 ml) extracted with 2N sodium hydroxide (3×1000 ml) the combined aqueous layer washed with diethyl ether (2×500 ml) Ice was then added to the aqueous layer followed by addition of 5N hydrochloric acid with cooling The oily suspension was stirred at room temperature overnight the solid filtered dried at room temperature under vacuum

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

実験手順: To a 500 ml 3-necked round bottom flask equipped with overhead mechanical stirrer, thermometer and nitrogen bubbler was charged 2-nitrobenzaldehyde (200 g, 1.32 mol) in methanol (1300 ml), to which was added isopropylamine (78.0 g, 113 ml, 1.32 mol) in one portion with stirring under nitrogen. The reaction mixture was then stirred for 100 minutes (followed reaction by GC), then added to a 4 litre stainless steel Parr hydrogenator, containing a suspension of 5% palladium on charcoal (13.24 g, 6% cat. loading) in methanol (500 ml) and the suspension hydrogenated under hydrogen at 60 psi for 3 hours. The suspension was filtered through a pad of celite, the pad washed with methanol (500 ml) and the combined filtrate evaporated under reduced pressure to leave a yellow oil, 2-amino-N-(1-methylethyl)-benzylamine. To a 500 ml 3-necked round bottom flask equipped with overhead mechanical stirrer The reaction mixture was then stirred for 100 minutes (followed reaction by GC) containing The suspension was filtered through a pad of celite the pad washed with methanol (500 ml) the combined filtrate evaporated under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir: