1-Benzyl-1,4-diazepan-5-one

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-Benzylhexahydro-(5H)-1,4-diazepine-5-one (1.5 g, 7.34 mmol) was dissolved in 12 mL of ethanol and 6 mL of acetic acid. After addition of 150 mg of 20% palladium hydroxide on carbon, the mixture was shaken under 40 psi of hydrogen for 4 h. The resulting mixture was centrifuged and the supernatant was filtered through a 0.45 micron membrane filter. The catalyst was washed with ethanol (3×10 mL), and the combined filtrate was concentrated in vacuo to give a yellow oil which began to crystallize. Swirling with 2 mL of methanol and 1 mL of ethyl acetate facilitated the crystallization, and evaporation of the solvent in vacuo gave 1.23 g (96%) of hexahydro-(5H)-1,4-diazepin-5-one acetic acid salt as light yellow crystals. the supernatant was filtered through a 0.45 micron membrane filter The catalyst was washed with ethanol (3×10 mL) the combined filtrate was concentrated in vacuo to give a yellow oil which to crystallize the crystallization, and evaporation of the solvent in vacuo

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

実験手順: 1-Benzylhexahydro-(5H)-1,4-diazepine-5-one (1.5 g, 7.34 mmol) was dissolved in 12 mL of ethanol and 6 mL of acetic acid. After addition of 150 mg of 20% palladium hydroxide on carbon, the mixture was shaken under 40 psi of hydrogen for 4 h. The resulting mixture was centrifuged and the supernatant was filtered through a 0.45 micron membrane filter. The catalyst was washed with ethanol (3×10 mL), and the combined filtrate was concentrated in vacuo to give a yellow oil which began to crystallize. Swirling with 2 mL of methanol and 1 mL of ethyl acetate facilitated the crystallization, and evaporation of the solvent in vacuo gave 1.23 g (96%) of hexahydro-(5H)-1,4-diazepin-5-one acetic acid salt as light yellow crystals. the supernatant was filtered through a 0.45 micron membrane filter The catalyst was washed with ethanol (3×10 mL) the combined filtrate was concentrated in vacuo to give a yellow oil which to crystallize the crystallization, and evaporation of the solvent in vacuo

反応条件: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 1-benzyl-1,4-diazepan-5-one (2.00 g, 9.80 mmol) in anhydrous dioxane (40 mL), sodium bicarbonate (8.81 g, 105 mmol) and phosphorus pentasulfide (2.92 g, 13.1 mmol) were added. The mixture was heated to 75° C. for 6 h. Dioxane was removed under reduced pressure and the residue was treated with water (80 mL). The resultant mixture was stirred at 50° C. for 1 h and then stirred an additional 2 h at 25° C. Sodium chloride (30.0 g) was added to the mixture and the aqueous phase was extracted with dichloromethane. The organic phase was concentrated to yield the desired compound, which was used without further purification. Dioxane was removed under reduced pressure the residue was treated with water (80 mL) stirred an additional 2 h at 25° C Sodium chloride (30.0 g) was added to the mixture the aqueous phase was extracted with dichloromethane The organic phase was concentrated

反応条件: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 1-benzyl-1,4-diazepan-5-one (2.00 g, 9.80 mmol) in anhydrous dioxane (40 mL), sodium bicarbonate (8.81 g, 105 mmol) and phosphorus pentasulfide (2.92 g, 13.1 mmol) were added. The mixture was heated to 75° C. for 6 h. Dioxane was removed under reduced pressure and the residue was treated with water (80 mL). The resultant mixture was stirred at 50° C. for 1 h and then stirred an additional 2 h at 25° C. Sodium chloride (30.0 g) was added to the mixture and the aqueous phase was extracted with dichloromethane. The organic phase was concentrated to yield the desired compound, which was used without further purification. Dioxane was removed under reduced pressure the residue was treated with water (80 mL) stirred an additional 2 h at 25° C Sodium chloride (30.0 g) was added to the mixture the aqueous phase was extracted with dichloromethane The organic phase was concentrated

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

実験手順: 1-Benzylhexahydro-(5H)-1,4-diazepine-5-one (1.5 g, 7.34 mmol) was dissolved in 12 mL of ethanol and 6 mL of acetic acid. After addition of 150 mg of 20% palladium hydroxide on carbon, the mixture was shaken under 40 psi of hydrogen for 4 h. The resulting mixture was centrifuged and the supernatant was filtered through a 0.45 micron membrane filter. The catalyst was washed with ethanol (3×10 mL), and the combined filtrate was concentrated in vacuo to give a yellow oil which began to crystallize. Swirling with 2 mL of methanol and 1 mL of ethyl acetate facilitated the crystallization, and evaporation of the solvent in vacuo gave 1.23 g (96%) of hexahydro-(5H)-1,4-diazepin-5-one acetic acid salt as light yellow crystals. the supernatant was filtered through a 0.45 micron membrane filter The catalyst was washed with ethanol (3×10 mL) the combined filtrate was concentrated in vacuo to give a yellow oil which to crystallize the crystallization, and evaporation of the solvent in vacuo

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

実験手順: 1M HCl in ethanol (7.2 mL) and 10% palladium-carbon (0.34 g) were added to 1-benzylhexahydro-1H-1,4-diazepin-5-one (1.490 g) in methanol (10 mL) at room temperature, and the resultant mixture was stirred in a hydrogen atmosphere for 4 hours. After the reaction atmosphere was purged with nitrogen, insoluble matter was removed by filtration. The solvent of the filtrate was evaporated under reduced pressure, and diethyl ether was added to the residue, and then the precipitated solid was recovered by filtration, to thereby give the title compound (1.045 g, 96%). After the reaction atmosphere was purged with nitrogen, insoluble matter was removed by filtration The solvent of the filtrate was evaporated under reduced pressure, and diethyl ether was added to the residue the precipitated solid was recovered by filtration

反応条件: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Concentrated sulfuric acid (25 mL) was added to 1-benzyl-4-piperidone (10.14 g) in acetic acid (50 mL) at room temperature, and sodium azide (3.880 g) was added thereto at 0° C. over a period of 2 hours, followed by stirring at 5° C. for 25 hours. The reaction mixture was alkalinized through addition of aqueous sodium hydroxide, followed by partitioning by use of chloroform. The aqueous layer was extracted with chloroform. The organic layers were combined, and washed with saturated brine, and then dried over sodium sulfate anhydrate, followed by filtration. The solvent was evaporated under reduced pressure, and then the residue was purified through silica gel column chromatography (chloroform-methanol), to thereby give the title compound as a solid (5.081 g, 47%). by partitioning by use of chloroform The aqueous layer was extracted with chloroform washed with saturated brine dried over sodium sulfate anhydrate followed by filtration The solvent was evaporated under reduced pressure the residue was purified through silica gel column chromatography (chloroform-methanol)

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

実験手順: 1-Benzylhexahydro-(5H)-1,4-diazepine-5-one (1.5 g, 7.34 mmol) was dissolved in 12 mL of ethanol and 6 mL of acetic acid. After addition of 150 mg of 20% palladium hydroxide on carbon, the mixture was shaken under 40 psi of hydrogen for 4 h. The resulting mixture was centrifuged and the supernatant was filtered through a 0.45 micron membrane filter. The catalyst was washed with ethanol (3×10 mL), and the combined filtrate was concentrated in vacuo to give a yellow oil which began to crystallize. Swirling with 2 mL of methanol and 1 mL of ethyl acetate facilitated the crystallization, and evaporation of the solvent in vacuo gave 1.23 g (96%) of hexahydro-(5H)-1,4-diazepin-5-one acetic acid salt as light yellow crystals. the supernatant was filtered through a 0.45 micron membrane filter The catalyst was washed with ethanol (3×10 mL) the combined filtrate was concentrated in vacuo to give a yellow oil which to crystallize the crystallization, and evaporation of the solvent in vacuo

反応条件: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 1-benzyl-1,4-diazepan-5-one (2.00 g, 9.80 mmol) in anhydrous dioxane (40 mL), sodium bicarbonate (8.81 g, 105 mmol) and phosphorus pentasulfide (2.92 g, 13.1 mmol) were added. The mixture was heated to 75° C. for 6 h. Dioxane was removed under reduced pressure and the residue was treated with water (80 mL). The resultant mixture was stirred at 50° C. for 1 h and then stirred an additional 2 h at 25° C. Sodium chloride (30.0 g) was added to the mixture and the aqueous phase was extracted with dichloromethane. The organic phase was concentrated to yield the desired compound, which was used without further purification. Dioxane was removed under reduced pressure the residue was treated with water (80 mL) stirred an additional 2 h at 25° C Sodium chloride (30.0 g) was added to the mixture the aqueous phase was extracted with dichloromethane The organic phase was concentrated