heptanedinitrile

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: 1,5-Dicyanopentane (Aldrich Chemicals) (25.0 g, 205 mmol), sodium hydride (60% oil dispersion; 8.2 g, 205 mmol) and T.H.F. (150 ml) were heated under reflux for 17 hours. After cooling, water (150 ml) was added and the upper organic layer removed, dried (Na2SO4) filtered and the solvent evaporated. Recrystallisation from hot toluene (80° C.) gave the product as beige crystals. (150 ml) were heated under reflux for 17 hours After cooling the upper organic layer removed dried (Na2SO4) filtered the solvent evaporated Recrystallisation from hot toluene (80° C.)

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A stirred mixture of 1,7-heptanedinitrile (24.44 g, 0.2 mol) and t-BuOK (22.44 g, 0.2 mol) was heated at 80° C. for 3 h under nitrogen. The mixture was then cooled down to room temperature and stored at that temperature overnight. The residue was treated with water, and extracted with ether (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by recrystallization from MeOH to give the title compound as a white solid (18.2 g, 75%). 1H NMR (400 MHz, CDCl3) δ 1.58-1.71 (m, 4H), 2.12-2.20 (m, 4H), 4.23 (bs, 2H). MS 123 (MH+). The mixture was then cooled down to room temperature stored at that temperature overnight extracted with ether (2×) The combined organic layers were washed with brine dried over Na2SO4 filtered concentrated The residue was purified by recrystallization from MeOH

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A stirred mixture of 1,7-heptanedinitrile (24.44 g, 0.2 mol) and t-BuOK (22.44 g, 0.2 mol) was heated at 80° C. for 3 h under nitrogen. The mixture was then cooled down to room temperature and stored at that temperature overnight. The residue was treated with water, and extracted with ether (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by recrystallization from MeOH to give the title compound as a white solid (18.2 g, 75%). 1H NMR (400 MHz, CDCl3) δ 1.58-1.71 (m, 4H), 2.12-2.20 (m, 4H), 4.23 (bs, 2H). MS 123 (MH+). The mixture was then cooled down to room temperature stored at that temperature overnight extracted with ether (2×) The combined organic layers were washed with brine dried over Na2SO4 filtered concentrated The residue was purified by recrystallization from MeOH

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A stirred mixture of 1,7-heptanedinitrile (24.44 g, 0.2 mol) and t-BuOK (22.44 g, 0.2 mol) was heated at 80° C. for 3 h under nitrogen. The mixture was then cooled down to room temperature and stored at that temperature overnight. The residue was treated with water, and extracted with ether (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by recrystallization from MeOH to give the title compound as a white solid (18.2 g, 75%). 1H NMR (400 MHz, CDCl3) δ 1.58-1.71 (m, 4H), 2.12-2.20 (m, 4H), 4.23 (bs, 2H). MS 123 (MH+). The mixture was then cooled down to room temperature stored at that temperature overnight extracted with ether (2×) The combined organic layers were washed with brine dried over Na2SO4 filtered concentrated The residue was purified by recrystallization from MeOH

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

実験手順: 1,5-Dicyanopentane (Aldrich Chemicals) (25.0 g, 205 mmol), sodium hydride (60% oil dispersion; 8.2 g, 205 mmol) and T.H.F. (150 ml) were heated under reflux for 17 hours. After cooling, water (150 ml) was added and the upper organic layer removed, dried (Na2SO4) filtered and the solvent evaporated. Recrystallisation from hot toluene (80° C.) gave the product as beige crystals. (150 ml) were heated under reflux for 17 hours After cooling the upper organic layer removed dried (Na2SO4) filtered the solvent evaporated Recrystallisation from hot toluene (80° C.)

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

実験手順: 1,5-Dicyanopentane (Aldrich Chemicals) (25.0 g, 205 mmol), sodium hydride (60% oil dispersion; 8.2 g, 205 mmol) and T.H.F. (150 ml) were heated under reflux for 17 hours. After cooling, water (150 ml) was added and the upper organic layer removed, dried (Na2SO4) filtered and the solvent evaporated. Recrystallisation from hot toluene (80° C.) gave the product as beige crystals. (150 ml) were heated under reflux for 17 hours After cooling the upper organic layer removed dried (Na2SO4) filtered the solvent evaporated Recrystallisation from hot toluene (80° C.)

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

実験手順: To cold toluene (20 mL) was added 60% NaH (720 mg, 18.0 mmol) slowly and followed by a solution of 1,5-dicyanopentane (2.1 mL, 16.37 mmol) in toluene (5 mL) slowly at 0° C. The resulting mixture was refluxed for 4 h and cooled to room temperature. The reaction mixture was quenched with ethanol (2 mL), water (20 mL) and acetic acid (2 mL). The organic layer was separated and aqueous layer was extracted with ethyl acetate (3×20 mL). The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. Water was added to the crude residue, then filtered and washed with hexane to afford 850 mg (42%) of 2-aminocyclohex-1-enecarbonitrile (I-7a) as a pale brown solid. The resulting mixture was refluxed for 4 h The reaction mixture was quenched with ethanol (2 mL), water (20 mL) and acetic acid (2 mL) The organic layer was separated aqueous layer was extracted with ethyl acetate (3×20 mL) The combined organic layer was washed with brine dried over anhydrous Na2SO4 concentrated under reduced pressure Water was added to the crude residue filtered washed with hexane

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A stirred mixture of 1,7-heptanedinitrile (24.44 g, 0.2 mol) and t-BuOK (22.44 g, 0.2 mol) was heated at 80° C. for 3 h under nitrogen. The mixture was then cooled down to room temperature and stored at that temperature overnight. The residue was treated with water, and extracted with ether (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by recrystallization from MeOH to give the title compound as a white solid (18.2 g, 75%). 1H NMR (400 MHz, CDCl3) δ1.58-1.71 (m, 4H), 2.12-2.20 (m, 4H), 4.23 (bs, 2H). MS 123 (MH+). The mixture was then cooled down to room temperature stored at that temperature overnight extracted with ether (2×) The combined organic layers were washed with brine dried over Na2SO4 filtered concentrated The residue was purified by recrystallization from MeOH

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

実験手順: To cold toluene (20 mL) was added 60% NaH (720 mg, 18.0 mmol) slowly and followed by a solution of 1,5-dicyanopentane (2.1 mL, 16.37 mmol) in toluene (5 mL) slowly at 0° C. The resulting mixture was refluxed for 4 h and cooled to room temperature. The reaction mixture was quenched with ethanol (2 mL), water (20 mL) and acetic acid (2 mL). The organic layer was separated and aqueous layer was extracted with ethyl acetate (3×20 mL). The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. Water was added to the crude residue, then filtered and washed with hexane to afford 850 mg (42%) of 2-aminocyclohex-1-enecarbonitrile (I-7a) as a pale brown solid. The resulting mixture was refluxed for 4 h The reaction mixture was quenched with ethanol (2 mL), water (20 mL) and acetic acid (2 mL) The organic layer was separated aqueous layer was extracted with ethyl acetate (3×20 mL) The combined organic layer was washed with brine dried over anhydrous Na2SO4 concentrated under reduced pressure Water was added to the crude residue filtered washed with hexane

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A stirred mixture of 1,7-heptanedinitrile (24.44 g, 0.2 mol) and t-BuOK (22.44 g, 0.2 mol) was heated at 80° C. for 3 h under nitrogen. The mixture was then cooled down to room temperature and stored at that temperature overnight. The residue was treated with water, and extracted with ether (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by recrystallization from MeOH to give the title compound as a white solid (18.2 g, 75%). 1H NMR (400 MHz, CDCl3) δ1.58-1.71 (m, 4H), 2.12-2.20 (m, 4H), 4.23 (bs, 2H). MS 123 (MH+). The mixture was then cooled down to room temperature stored at that temperature overnight extracted with ether (2×) The combined organic layers were washed with brine dried over Na2SO4 filtered concentrated The residue was purified by recrystallization from MeOH

反応条件: temp:0.00; pressure:0.00; stir: