4-(2-methylprop-1-enyl)morpholine

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

実験手順: A 1.88 g. portion of 3,4-dichlorophenylisocyanate was added to 2.82 g. of 1-morpholino-1-isobutene. The mixture was stirred at room temperature for 48 hours. At the end of that time, the excess enamine was removed under vacuum, and the remaining oil, 3.0 g., was found by nuclear magnetic resonance analysis to be 1-(3,4-dichlorophenyl)-3,3-dimethyl-4-morpholino-2-azetidinone, a liquid. At the end of that time, the excess enamine was removed under vacuum

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

実験手順: A 1.88 g. portion of 3,4-dichlorophenylisocyanate was added to 2.82 g. of 1-morpholino-1-isobutene. The mixture was stirred at room temperature for 48 hours. At the end of that time, the excess enamine was removed under vacuum, and the remaining oil, 3.0 g., was found by nuclear magnetic resonance analysis to be 1-(3,4-dichlorophenyl)-3,3-dimethyl-4-morpholino-2-azetidinone, a liquid. At the end of that time, the excess enamine was removed under vacuum

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

実験手順: Isobutyraldehyde (19.4 g; 0.27 mol) is added slowly with stirring to morpholine (21.75 g; 0.25 mol). The ensuing reaction is exothermic. On completion of the addition the reaction mixture is stirred and heated at reflux for 5 hours while water (4.1 ml) is being azeotroped out of it. The reaction mixture is then vacuum distilled. A fraction collected at 64°-67° C. and 13 mm Hg weighs 15.6 g and consists of 90% by weight of title product and 10% by weight of morpholine. A second fraction collected at 67°-67.5° C. and 13 mm Hg (lit. 56°-57° C.; 11 mm Hg) weighs 16.2 g (46%) and is shown to be pure title product by nuclear magnetic resonance (nmr) and infrared (ir). The ensuing reaction On completion of the addition the reaction mixture heated is being azeotroped out of it vacuum distilled A fraction collected at 64°-67° C. A second fraction collected at 67°-67.5° C. 13 mm Hg (lit. 56°-57° C.; 11 mm Hg)

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

実験手順: Isobutyraldehyde (19.4 g; 0.27 mol) is added slowly with stirring to morpholine (21.75 g; 0.25 mol). The ensuing reaction is exothermic. On completion of the addition the reaction mixture is stirred and heated at reflux for 5 hours while water (4.1 ml) is being azeotroped out of it. The reaction mixture is then vacuum distilled. A fraction collected at 64°-67° C. and 13 mm Hg weighs 15.6 g and consists of 90% by weight of title product and 10% by weight of morpholine. A second fraction collected at 67°-67.5° C. and 13 mm Hg (lit. 56°-57° C.; 11 mm Hg) weighs 16.2 g (46%) and is shown to be pure title product by nuclear magnetic resonance (nmr) and infrared (ir). The ensuing reaction On completion of the addition the reaction mixture heated is being azeotroped out of it vacuum distilled A fraction collected at 64°-67° C. A second fraction collected at 67°-67.5° C. 13 mm Hg (lit. 56°-57° C.; 11 mm Hg)

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

実験手順: Morpholine (21.78 g, 0.25 mol) and isobutyraldehyde (18.02 g, 0.25 mol) were heated to reflux as a neat mixture, in a 100 ml round bottom flask with a Dean Stark Trap attached. After the mixture was refluxed overnight, the reaction mixture was purified by vacuum distillation. The pure enamine product (15.01 g, 0.10 mol, 42%) had a 1H-NMR (CDCl3): 5.32 (s, 1H), 3.72 (t, 4H), 2.87 (t, 4H), 1.81 (s, 3H), 1.68 (s, 3H) It had LC-MS (ES+): 142 [MH]+ m/e. to reflux as a neat mixture, in a 100 ml round bottom flask with a Dean Stark Trap After the mixture was refluxed overnight the reaction mixture was purified by vacuum distillation

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

実験手順: Morpholine (21.78 g, 0.25 mol) and isobutyraldehyde (18.02 g, 0.25 mol) were heated to reflux as a neat mixture, in a 100 ml round bottom flask with a Dean Stark Trap attached. After the mixture was refluxed overnight, the reaction mixture was purified by vacuum distillation. The pure enamine product (15.01 g, 0.10 mol, 42%) had a 1H-NMR (CDCl3): 5.32 (s, 1H), 3.72 (t, 4H), 2.87 (t, 4H), 1.81 (s, 3H), 1.68 (s, 3H) It had LC-MS (ES+): 142 [MH]+ m/e. to reflux as a neat mixture, in a 100 ml round bottom flask with a Dean Stark Trap After the mixture was refluxed overnight the reaction mixture was purified by vacuum distillation

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

実験手順: 210 g (1.5 mols) of 1-morpholino-2-methyl-prop-1-ene are added dropwise, in the course of one hour, to 169.0 g (1.5 mols) of chloroacetyl chloride, dissolved in 350 ml of diethyl ether, at 5° C. After the addition is complete, the mixture is stirred for a further 3 hours under reflux. The solution is poured onto 100 g of ice and brought to pH 5 with aqueous sodium bicarbonate solution, and the ether phase is separated off. The aqueous phase is extracted with 100 ml of diethyl ether, the organic phases are combined, and dried over sodium sulphate, the solvent is distilled off and the residue is distilled under the vacuum from a water jet. 136.4 g (61% of theory) of 4-chloro-3-keto-2,2-dimethylbutanal of boiling point 95°-98° C./14 mbar are obtained. After the addition under reflux the ether phase is separated off The aqueous phase is extracted with 100 ml of diethyl ether dried over sodium sulphate the solvent is distilled off the residue is distilled under the vacuum from a water jet

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

実験手順: A 1.88 g. portion of 3,4-dichlorophenylisocyanate was added to 2.82 g. of 1-morpholino-1-isobutene. The mixture was stirred at room temperature for 48 hours. At the end of that time, the excess enamine was removed under vacuum, and the remaining oil, 3.0 g., was found by nuclear magnetic resonance analysis to be 1-(3,4-dichlorophenyl)-3,3-dimethyl-4-morpholino-2-azetidinone, a liquid. At the end of that time, the excess enamine was removed under vacuum

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

実験手順: Isobutyraldehyde (19.4 g; 0.27 mol) is added slowly with stirring to morpholine (21.75 g; 0.25 mol). The ensuing reaction is exothermic. On completion of the addition the reaction mixture is stirred and heated at reflux for 5 hours while water (4.1 ml) is being azeotroped out of it. The reaction mixture is then vacuum distilled. A fraction collected at 64°-67° C. and 13 mm Hg weighs 15.6 g and consists of 90% by weight of title product and 10% by weight of morpholine. A second fraction collected at 67°-67.5° C. and 13 mm Hg (lit. 56°-57° C.; 11 mm Hg) weighs 16.2 g (46%) and is shown to be pure title product by nuclear magnetic resonance (nmr) and infrared (ir). The ensuing reaction On completion of the addition the reaction mixture heated is being azeotroped out of it vacuum distilled A fraction collected at 64°-67° C. A second fraction collected at 67°-67.5° C. 13 mm Hg (lit. 56°-57° C.; 11 mm Hg)