3-(3,5-difluorophenyl)propan-1-amine

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

実験手順: A solution of 3-(3,5-difluorophenyl)propylamine (0.0327 mol) and triethylamine (0.072 mol) in tetrahydrofuran (20 ml) was added dropwise to a solution of thiophosgene (0.0392 mol) in tetrahydrofuran at 0°. The reaction was stirred 2 hours at room temperature then ethyl ether was added and the mixture filtered. The filtrate was concentrated and distilled (Kugelrohr) to yield 3.8 g (55%) of a yellow oil. the mixture filtered The filtrate was concentrated distilled (Kugelrohr)

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

実験手順: A solution of 3-(3,5-difluorophenyl)propylamine (0.0327 mol) and triethylamine (0.072 mol) in tetrahydrofuran (20 ml) was added dropwise to a solution of thiophosgene (0.0392 mol) in tetrahydrofuran at 0°. The reaction was stirred 2 hours at room temperature then ethyl ether was added and the mixture filtered. The filtrate was concentrated and distilled (Kugelrohr) to yield 3.8 g (55%) of a yellow oil. the mixture filtered The filtrate was concentrated distilled (Kugelrohr)

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

実験手順: 3-(3,5-Difluorophenyl)propylazide (0.034 mol) in methanol (75 ml) was shaken with a slurry of methanol washed Raney nickel under 50 psi hydrogen for 2 hours. The reaction mixture was filtered and the filtrate concentrated to yield 5.6 g (96%) of an oily product. washed Raney nickel under 50 psi hydrogen for 2 hours The reaction mixture was filtered the filtrate concentrated

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

実験手順: 3-(3,5-Difluorophenyl)propylazide (0.034 mol) in methanol (75 ml) was shaken with a slurry of methanol washed Raney nickel under 50 psi hydrogen for 2 hours. The reaction mixture was filtered and the filtrate concentrated to yield 5.6 g (96%) of an oily product. washed Raney nickel under 50 psi hydrogen for 2 hours The reaction mixture was filtered the filtrate concentrated

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

実験手順: Condensation of 3-(3,5-difluorophenyl)-1-propylamine (1.5 g, 6.5 mmol) and ketone 5 (1.5 g, 6.5 mmol), following the procedure described in Example 1, gave 6-(trans-4-[3-(3,5-difluorophenyl)propylamino]cyclohexyl}-3H-benzoxazol-2-one (640 mg, 26%), as a white solid: 1H NMR (500 MHz, DMSO-d6): δ 7.13 (s, 1H), 7.01-6.92 (m, 5H), 2.66 (t, J=8 Hz, 2H), 2.57 (t, J=8 Hz, 2H), 2.49-2.40 (m, 2H), 1.95 (br d, J=10 Hz, 2H), 1.78 (br d, J=10 Hz, 2H), 1.74-1.68 (m, 2H), 1.45 (dddd, J=13, 13, 13, 3 Hz, 2H), 1.14 (dddd, J=13, 13, 13, 3 Hz, 2H).

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

実験手順: Condensation of 3-(3,5-difluorophenyl)-1-propylamine (1.5 g, 6.5 mmol) and ketone 5 (1.5 g, 6.5 mmol), following the procedure described in Example 1, gave 6-(trans-4-[3-(3,5-difluorophenyl)propylamino]cyclohexyl}-3H-benzoxazol-2-one (640 mg, 26%), as a white solid: 1H NMR (500 MHz, DMSO-d6): δ 7.13 (s, 1H), 7.01-6.92 (m, 5H), 2.66 (t, J=8 Hz, 2H), 2.57 (t, J=8 Hz, 2H), 2.49-2.40 (m, 2H), 1.95 (br d, J=10 Hz, 2H), 1.78 (br d, J=10 Hz, 2H), 1.74-1.68 (m, 2H), 1.45 (dddd, J=13, 13, 13, 3 Hz, 2H), 1.14 (dddd, J=13, 13, 13, 3 Hz, 2H).

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

実験手順: A solution of 3-(3,5-difluorophenyl)propylamine (0.0327 mol) and triethylamine (0.072 mol) in tetrahydrofuran (20 ml) was added dropwise to a solution of thiophosgene (0.0392 mol) in tetrahydrofuran at 0°. The reaction was stirred 2 hours at room temperature then ethyl ether was added and the mixture filtered. The filtrate was concentrated and distilled (Kugelrohr) to yield 3.8 g (55%) of a yellow oil. the mixture filtered The filtrate was concentrated distilled (Kugelrohr)

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

実験手順: 3-(3,5-Difluorophenyl)propylazide (0.034 mol) in methanol (75 ml) was shaken with a slurry of methanol washed Raney nickel under 50 psi hydrogen for 2 hours. The reaction mixture was filtered and the filtrate concentrated to yield 5.6 g (96%) of an oily product. washed Raney nickel under 50 psi hydrogen for 2 hours The reaction mixture was filtered the filtrate concentrated

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

実験手順: A solution of 3-(3,5-difluorophenyl)propylamine (0.0327 mol) and triethylamine (0.072 mol) in tetrahydrofuran (20 ml) was added dropwise to a solution of thiophosgene (0.0392 mol) in tetrahydrofuran at 0°. The reaction was stirred 2 hours at room temperature then ethyl ether was added and the mixture filtered. The filtrate was concentrated and distilled (Kugelrohr) to yield 3.8 g (55%) of a yellow oil. the mixture filtered The filtrate was concentrated distilled (Kugelrohr)

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

実験手順: 3-(3,5-Difluorophenyl)propylazide (0.034 mol) in methanol (75 ml) was shaken with a slurry of methanol washed Raney nickel under 50 psi hydrogen for 2 hours. The reaction mixture was filtered and the filtrate concentrated to yield 5.6 g (96%) of an oily product. washed Raney nickel under 50 psi hydrogen for 2 hours The reaction mixture was filtered the filtrate concentrated

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

実験手順: Condensation of 3-(3,5-difluorophenyl)-1-propylamine (1.5 g, 6.5 mmol) and ketone 5 (1.5 g, 6.5 mmol), following the procedure described in Example 1, gave 6-(trans-4-[3-(3,5-difluorophenyl)propylamino]cyclohexyl}-3H-benzoxazol-2-one (640 mg, 26%), as a white solid: 1H NMR (500 MHz, DMSO-d6): δ 7.13 (s, 1H), 7.01-6.92 (m, 5H), 2.66 (t, J=8 Hz, 2H), 2.57 (t, J=8 Hz, 2H), 2.49-2.40 (m, 2H), 1.95 (br d, J=10 Hz, 2H), 1.78 (br d, J=10 Hz, 2H), 1.74-1.68 (m, 2H), 1.45 (dddd, J=13, 13, 13, 3 Hz, 2H), 1.14 (dddd, J=13, 13, 13, 3 Hz, 2H).

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

実験手順: A solution of 3-(3,5-difluorophenyl)propylamine (0.0327 mol) and triethylamine (0.072 mol) in tetrahydrofuran (20 ml) was added dropwise to a solution of thiophosgene (0.0392 mol) in tetrahydrofuran at 0°. The reaction was stirred 2 hours at room temperature then ethyl ether was added and the mixture filtered. The filtrate was concentrated and distilled (Kugelrohr) to yield 3.8 g (55%) of a yellow oil. the mixture filtered The filtrate was concentrated distilled (Kugelrohr)