2-氮杂环壬酮

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:105.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A 5 L three-neck round bottom flask was fitted with a heating mantle, an overhead mechanical stirrer, an addition funnel, and a thermometer. The reaction was performed under an argon atmosphere. Hydroxylamine-O-sulfonic acid (196.7 g, 1.74 moles, 1.10 equiv.) and formic acid (1 L) were charged into the round bottom flask and stirred to form a white slurry. A solution of cyclooctanone (200.0 g 1.58 moles, 1.0 equiv.) in formic acid (600 mL) was added dropwise to the white slurry via the addition funnel. After the addition, the addition funnel was replaced by a reflux condenser, and the reaction was heated to reflux (internal temperature about 105° C.) for 1 hour to give a brown solution. After the solution was cooled to room temperature, it was poured into a mixture of saturated aqueous ammonium chloride (1.5 L) and water (1.5 L). The aqueous mixture was extracted with chloroform (3×1200 mL). The combined chloroform layers were transferred into a beaker, and saturated sodium bicarbonate (2 L) was added slowly. The chloroform layer was then separated, dried over anhydrous sodium sulfate, and evaporated under reduced pressure to afford a brown oil. The oil was placed in a 500 mL round bottom flask with a magnetic stirrer. The round bottom flask was placed in a silicon oil bath and was fitted with a short path vacuum distillation head equipped with a thermometer. A Cow-type receiver was connected to three 250 mL flasks. 2-Azacyclononanone (145 g, 65%, mp 64°-69° C.) was obtained by vacuum distillation (fraction with head temperature range from 80°- to 120° C at pressures between 3.0 and 3.4 mmHg). A 5 L three-neck round bottom flask was fitted with a heating mantle, an overhead mechanical stirrer, an addition funnel to form a white slurry After the addition the addition funnel was replaced by a reflux condenser the reaction was heated to give a brown solution After the solution was cooled to room temperature The aqueous mixture was extracted with chloroform (3×1200 mL) was added slowly The chloroform layer was then separated dried over anhydrous sodium sulfate evaporated under reduced pressure to afford a brown oil The oil was placed in a 500 mL round bottom flask with a magnetic stirrer The round bottom flask was placed in a silicon oil bath was fitted with a short path vacuum distillation head equipped with a thermometer

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Following example 17, 4.2 g of 50% sodium hydride-mineral oil dispersion (2.1 g NaH, 0.0875 M), 10 g (0.0708 M) of azacyclononan-2-one and 15 g (0.0777 M) of 1-bromooctane gave 12.5 g (70%) of product; b.p. 150°-160°/0.5 mm.

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Following example 10, 16.32 g of 50% sodium hydride-mineral oil dispersion (8.16 g NaH, 0.34 M), 40 g (0.283 M) of azacyclononan-2-one and 43 g (0.311 M) of 1-bromobutane was refluxed for 22 hours. The reaction mixture was diluted with benzene-tolune and was extracted with water. The organic phase was separated, dried and concentrated to a yellow oil. Distillation afforded 41.4 g (74%) of product; b.p. 166°-170°/0.2 mm. was refluxed for 22 hours was extracted with water The organic phase was separated dried concentrated to a yellow oil Distillation

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 0.3 mol % of sodium hydride and 0.3 mol % of the co-catalyst according to the Example 15 were dissolved in molten laurolactam. After 120 minutes at 160°C the polymerizate contained almost the equilibrium amount of the polyamide. Similar result was obtained with caprylolactam. Similar result

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 0.3 mol % of sodium hydride and 0.3 mol % of the co-catalyst according to the Example 15 were dissolved in molten laurolactam. After 120 minutes at 160°C the polymerizate contained almost the equilibrium amount of the polyamide. Similar result was obtained with caprylolactam. Similar result

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 0.3 mol % of sodium hydride and 0.3 mol % of the co-catalyst according to the Example 15 were dissolved in molten laurolactam. After 120 minutes at 160°C the polymerizate contained almost the equilibrium amount of the polyamide. Similar result was obtained with caprylolactam. Similar result

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 0.3 mol % of sodium hydride and 0.3 mol % of the co-catalyst according to the Example 15 were dissolved in molten laurolactam. After 120 minutes at 160°C the polymerizate contained almost the equilibrium amount of the polyamide. Similar result was obtained with caprylolactam. Similar result

反应条件: temp:105.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A 5 L three-neck round bottom flask was fitted with a heating mantle, an overhead mechanical stirrer, an addition funnel, and a thermometer. The reaction was performed under an argon atmosphere. Hydroxylamine-O-sulfonic acid (196.7 g, 1.74 moles, 1.10 equiv.) and formic acid (1 L) were charged into the round bottom flask and stirred to form a white slurry. A solution of cyclooctanone (200.0 g 1.58 moles, 1.0 equiv.) in formic acid (600 mL) was added dropwise to the white slurry via the addition funnel. After the addition, the addition funnel was replaced by a reflux condenser, and the reaction was heated to reflux (internal temperature about 105° C.) for 1 hour to give a brown solution. After the solution was cooled to room temperature, it was poured into a mixture of saturated aqueous ammonium chloride (1.5 L) and water (1.5 L). The aqueous mixture was extracted with chloroform (3×1200 mL). The combined chloroform layers were transferred into a beaker, and saturated sodium bicarbonate (2 L) was added slowly. The chloroform layer was then separated, dried over anhydrous sodium sulfate, and evaporated under reduced pressure to afford a brown oil. The oil was placed in a 500 mL round bottom flask with a magnetic stirrer. The round bottom flask was placed in a silicon oil bath and was fitted with a short path vacuum distillation head equipped with a thermometer. A Cow-type receiver was connected to three 250 mL flasks. 2-Azacyclononanone (145 g, 65%, mp 64°-69° C.) was obtained by vacuum distillation (fraction with head temperature range from 80° to 120° C. at pressures between 3.0 and 3.4 mmHg). A 5 L three-neck round bottom flask was fitted with a heating mantle, an overhead mechanical stirrer, an addition funnel to form a white slurry After the addition the addition funnel was replaced by a reflux condenser the reaction was heated to give a brown solution After the solution was cooled to room temperature The aqueous mixture was extracted with chloroform (3×1200 mL) was added slowly The chloroform layer was then separated dried over anhydrous sodium sulfate evaporated under reduced pressure to afford a brown oil The oil was placed in a 500 mL round bottom flask with a magnetic stirrer The round bottom flask was placed in a silicon oil bath was fitted with a short path vacuum distillation head equipped with a thermometer

反应条件: temp:105.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A 5 L three-neck round bottom flask was fitted with a heating mantle, an overhead mechanical stirrer, an addition funnel, and a thermometer. The reaction was performed under an argon atmosphere. Hydroxylamine-O-sulfonic acid (196.7 g, 1.74 moles, 1.10 equiv.) and formic acid (1 L) were charged into the round bottom flask and stirred to form a white slurry. A solution of cyclooctanone (200.0 g 1.58 moles, 1.0 equiv.) in formic acid (600 mL) was added dropwise to the white slurry via the addition funnel. After the addition, the addition funnel was replaced by a reflux condenser, and the reaction was heated to reflux (internal temperature about 105° C.) for 1 hour to give a brown solution. After the solution was cooled to room temperature, it was poured into a mixture of saturated aqueous ammonium chloride (1.5 L) and water (1.5 L). The aqueous mixture was extracted with chloroform (3×1200 mL). The combined chloroform layers were transferred into a beaker, and saturated sodium bicarbonate (2 L) was added slowly. The chloroform layer was then separated, dried over anhydrous sodium sulfate, and evaporated under reduced pressure to afford a brown oil. The oil was placed in a 500 mL round bottom flask with a magnetic stirrer. The round bottom flask was placed in a silicon oil bath and was fitted with a short path vacuum distillation head equipped with a thermometer. A Cow-type receiver was connected to three 250 mL flasks. 2-Azacyclononanone (145 g, 65%, mp 64°-69° C.) was obtained by vacuum distillation (fraction with head temperature range from 80° to 120° C. at pressures between 3.0 and 3.4 mmHg). A 5 L three-neck round bottom flask was fitted with a heating mantle, an overhead mechanical stirrer, an addition funnel to form a white slurry After the addition the addition funnel was replaced by a reflux condenser the reaction was heated to give a brown solution After the solution was cooled to room temperature The aqueous mixture was extracted with chloroform (3×1200 mL) was added slowly The chloroform layer was then separated dried over anhydrous sodium sulfate evaporated under reduced pressure to afford a brown oil The oil was placed in a 500 mL round bottom flask with a magnetic stirrer The round bottom flask was placed in a silicon oil bath was fitted with a short path vacuum distillation head equipped with a thermometer

反应条件: temp:105.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A 5 L three-neck round bottom flask was fitted with a heating mantle, an overhead mechanical stirrer, an addition funnel, and a thermometer. The reaction was performed under an argon atmosphere. Hydroxylamine-O-sulfonic acid (196.7 g, 1.74 moles, 1.10 equiv.) and formic acid (1 L) were charged into the round bottom flask and stirred to form a white slurry. A solution of cyclooctanone (200.0 g 1.58 moles, 1.0 equiv.) in formic acid (600 mL) was added dropwise to the white slurry via the addition funnel. After the addition, the addition funnel was replaced by a reflux condenser, and the reaction was heated to reflux (internal temperature about 105° C.) for 1 hour to give a brown solution. After the solution was cooled to room temperature, it was poured into a mixture of saturated aqueous ammonium chloride (1.5 L) and water (1.5 L). The aqueous mixture was extracted with chloroform (3×1200 mL). The combined chloroform layers were transferred into a beaker, and saturated sodium bicarbonate (2 L) was added slowly. The chloroform layer was then separated, dried over anhydrous sodium sulfate, and evaporated under reduced pressure to afford a brown oil. The oil was placed in a 500 mL round bottom flask with a magnetic stirrer. The round bottom flask was placed in a silicon oil bath and was fitted with a short path vacuum distillation head equipped with a thermometer. A Cow-type receiver was connected to three 250 mL flasks. 2-Azacyclononanone (145 g, 65%, mp 64-69° C.) was obtained by vacuum distillation (fraction with head temperature range from 80 to 120° C. at pressures between 3.0 and 3.4 mmHg). A 5 L three-neck round bottom flask was fitted with a heating mantle, an overhead mechanical stirrer, an addition funnel to form a white slurry After the addition the addition funnel was replaced by a reflux condenser the reaction was heated to give a brown solution After the solution was cooled to room temperature The aqueous mixture was extracted with chloroform (3×1200 mL) was added slowly The chloroform layer was then separated dried over anhydrous sodium sulfate evaporated under reduced pressure to afford a brown oil The oil was placed in a 500 mL round bottom flask with a magnetic stirrer The round bottom flask was placed in a silicon oil bath was fitted with a short path vacuum distillation head equipped with a thermometer

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Caprylolactam (Fluka, N.Y., #21631) (25 g, 117 mmoles) is combined with lithium aluminum hydride (10.5 g) in ether and reduced with stirring for 5 hr. The reaction mixture is filtered and evaporated with ether. The product is octahydroazonin (90% yield). The reaction mixture is filtered evaporated with ether