3-(2,4-difluorophenyl)propan-1-amine

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:

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: Coupling of ketone 5 and 3-(2,4-difluorophenyl)-1-propylamine, using the method given in Example 1, gave (a) 6-{trans-4-[3-(2,4-difluorophenyl)-propylamino]-cyclohexyl}-3H-benzoxazol-2-one and (0.75 g, 37%), isolated as the HCl salt: 1H NMR (500 MHz, DMSO-d6): δ 11.49 (s, 1H), 8.84 (br s, 2H), 7.40 (ddd, J=9, 9, 7 Hz, 1H), 7.22-7.18 (m, 2H), 7.05 (ddd, J=8, 8, 2 Hz, 1H), 7.01 (dd, J=8, 1 Hz, 1H), 6.99 (d, J=8 Hz, 1H), 3.11-3.02 (m, 1H), 2.98-2.92 (m, 2H), 2.70 (t, J=8 Hz, 2H), 2.56-2.49 (m, 1H), 2.18-2.11 (m, 2H), 1.96-1.86 (m, 4H), 1.51 (m, 4H), and

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

実験手順: Coupling of ketone 5 and 3-(2,4-difluorophenyl)-1-propylamine, using the method given in Example 1, gave (a) 6-{trans-4-[3-(2,4-difluorophenyl)-propylamino]-cyclohexyl}-3H-benzoxazol-2-one and (0.75 g, 37%), isolated as the HCl salt: 1H NMR (500 MHz, DMSO-d6): δ 11.49 (s, 1H), 8.84 (br s, 2H), 7.40 (ddd, J=9, 9, 7 Hz, 1H), 7.22-7.18 (m, 2H), 7.05 (ddd, J=8, 8, 2 Hz, 1H), 7.01 (dd, J=8, 1 Hz, 1H), 6.99 (d, J=8 Hz, 1H), 3.11-3.02 (m, 1H), 2.98-2.92 (m, 2H), 2.70 (t, J=8 Hz, 2H), 2.56-2.49 (m, 1H), 2.18-2.11 (m, 2H), 1.96-1.86 (m, 4H), 1.51 (m, 4H), and

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

実験手順: 17.1 g (0.10 mol) of 3-(2,4-difluorophenyl)propylamine are heated at 260° C. for 2 hours in an autoclave with 13.2 g (0.10 mol) of 2,4-dimethoxytetrahydrofuran. The reaction mixture is cooled and then purified by vacuum distillation. 10.6 g (48% of theory) of a colourless oil which boils at 80° C. and 0.2 mbar or 146°-147° C. and 15 mbar are obtained. The reaction mixture is cooled purified by vacuum distillation 10.6 g (48% of theory) of a colourless oil which boils at 80° C. and 0.2 mbar or 146°-147° C. and 15 mbar are obtained

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

実験手順: 33.4 g (0.20 mol) of 3-(2,4-difluorophenyl)propionitrile are dissolved in 200 ml of ethanol and, after 2.8 g of Raney nickel in ethanol have been added and after 34 g (2.0 mol) of ammonia gas have been injected, are hydrogenated using hydrogen gas in a pressurized reactor at 75°-80° C. The take-up of hydrogen is complete after about 3 hours. The reaction mixture is cooled, decompressed and filtered and then freed from solvent on a vacuum rotary evaporator. The resultant oil is subjected to fractional distillation at 89°-90° C. in vacuo (13 mbar). 26.0 g (76% of theory) of a colourless oil are obtained. at 75°-80° C The reaction mixture is cooled filtered freed from solvent on a vacuum rotary evaporator The resultant oil is subjected to fractional distillation at 89°-90° C. in vacuo (13 mbar) 26.0 g (76% of theory) of a colourless oil are obtained

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

実験手順: 33.4 g (0.20 mol) of 3-(2,4-difluorophenyl)propionitrile are dissolved in 200 ml of ethanol and, after 2.8 g of Raney nickel in ethanol have been added and after 34 g (2.0 mol) of ammonia gas have been injected, are hydrogenated using hydrogen gas in a pressurized reactor at 75°-80° C. The take-up of hydrogen is complete after about 3 hours. The reaction mixture is cooled, decompressed and filtered and then freed from solvent on a vacuum rotary evaporator. The resultant oil is subjected to fractional distillation at 89°-90° C. in vacuo (13 mbar). 26.0 g (76% of theory) of a colourless oil are obtained. at 75°-80° C The reaction mixture is cooled filtered freed from solvent on a vacuum rotary evaporator The resultant oil is subjected to fractional distillation at 89°-90° C. in vacuo (13 mbar) 26.0 g (76% of theory) of a colourless oil are obtained

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

実験手順: Coupling of ketone 5 and 3-(2,4-difluorophenyl)-1-propylamine, using the method given in Example 1, gave (a) 6-{trans-4-[3-(2,4-difluorophenyl)-propylamino]-cyclohexyl}-3H-benzoxazol-2-one and (0.75 g, 37%), isolated as the HCl salt: 1H NMR (500 MHz, DMSO-d6): δ 11.49 (s, 1H), 8.84 (br s, 2H), 7.40 (ddd, J=9, 9, 7 Hz, 1H), 7.22-7.18 (m, 2H), 7.05 (ddd, J=8, 8, 2 Hz, 1H), 7.01 (dd, J=8, 1 Hz, 1H), 6.99 (d, J=8 Hz, 1H), 3.11-3.02 (m, 1H), 2.98-2.92 (m, 2H), 2.70 (t, J=8 Hz, 2H), 2.56-2.49 (m, 1H), 2.18-2.11 (m, 2H), 1.96-1.86 (m, 4H), 1.51 (m, 4H), and

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

実験手順: 17.1 g (0.10 mol) of 3-(2,4-difluorophenyl)propylamine are heated at 260° C. for 2 hours in an autoclave with 13.2 g (0.10 mol) of 2,4-dimethoxytetrahydrofuran. The reaction mixture is cooled and then purified by vacuum distillation. 10.6 g (48% of theory) of a colourless oil which boils at 80° C. and 0.2 mbar or 146°-147° C. and 15 mbar are obtained. The reaction mixture is cooled purified by vacuum distillation 10.6 g (48% of theory) of a colourless oil which boils at 80° C. and 0.2 mbar or 146°-147° C. and 15 mbar are obtained

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

実験手順: 33.4 g (0.20 mol) of 3-(2,4-difluorophenyl)propionitrile are dissolved in 200 ml of ethanol and, after 2.8 g of Raney nickel in ethanol have been added and after 34 g (2.0 mol) of ammonia gas have been injected, are hydrogenated using hydrogen gas in a pressurized reactor at 75°-80° C. The take-up of hydrogen is complete after about 3 hours. The reaction mixture is cooled, decompressed and filtered and then freed from solvent on a vacuum rotary evaporator. The resultant oil is subjected to fractional distillation at 89°-90° C. in vacuo (13 mbar). 26.0 g (76% of theory) of a colourless oil are obtained. at 75°-80° C The reaction mixture is cooled filtered freed from solvent on a vacuum rotary evaporator The resultant oil is subjected to fractional distillation at 89°-90° C. in vacuo (13 mbar) 26.0 g (76% of theory) of a colourless oil are obtained