4-N,4-N-dimethylcyclohexane-1,4-diamine

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

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: A mixture of 68 g of 4-dimethylaminoaniline and 34 g of 5% palladium-on-charcoal in 250 ml of AcOH is hydrogenated at a temperature of 75°-90° C. under a pressure of 50 bar. The catalyst is filtered off and washed with water and the filtrate is evaporated under vacuum. The residue is taken up with water, rendered alkaline by the addition of concentrated NaOH, extracted with AcOEt and dried over Na2SO4 and the solvent is evaporated off under vacuum. The oil obtained is distilled under reduced pressure to give 16.2 g of the expected product in the form of an oil. B.p.=102°-110° C. under 20 mm Hg. is hydrogenated at a temperature of 75°-90° C. under a pressure of 50 bar The catalyst is filtered off washed with water the filtrate is evaporated under vacuum by the addition of concentrated NaOH extracted with AcOEt dried over Na2SO4 the solvent is evaporated off under vacuum The oil obtained is distilled under reduced pressure

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

実験手順: A mixture of 68 g of 4-dimethylaminoaniline and 34 g of 5% palladium-on-charcoal in 250 ml of AcOH is hydrogenated at a temperature of 75°-90° C. under a pressure of 50 bar. The catalyst is filtered off and washed with water and the filtrate is evaporated under vacuum. The residue is taken up with water, rendered alkaline by the addition of concentrated NaOH, extracted with AcOEt and dried over Na2SO4 and the solvent is evaporated off under vacuum. The oil obtained is distilled under reduced pressure to give 16.2 g of the expected product in the form of an oil. B.p.=102°-110° C. under 20 mm Hg. is hydrogenated at a temperature of 75°-90° C. under a pressure of 50 bar The catalyst is filtered off washed with water the filtrate is evaporated under vacuum by the addition of concentrated NaOH extracted with AcOEt dried over Na2SO4 the solvent is evaporated off under vacuum The oil obtained is distilled under reduced pressure

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

実験手順: 4-(1-Methyl-1,2,3,4-tetrazol-5-yl)thio-butyric acid (45 mmole) is dissolved in tetrahydrofuran (50 ml), and thereto is added DBU (50 mmole). To the mixture is added dropwise with stirring isobutyl chloroformate (50 mmole) under ice-cooling, and the mixture is stirred at room temperature for 30 minutes. To the mixture is added dropwise 4-(N,N-dimethylamino)cyclohexylamine (54 mmole), and the mixture is further stirred at room temperature for 2 hours. After distilling off the solvent under reduced pressure, the resulting residue is extracted with chloroform. The chloroform layer is washed with 5% aqueous hydrochloric acid, an aqueous saturated sodium hydrogen carbonate solution and an aqueous saturated sodium chloride solution and then dried over anhydrous sodium sulfate. Chloroform is distilled off, and the resulting residue is subjected to silica gel column chromatography (Wakogel C-200, eluting solvent, benzene:chloroform=4:1, V/V) to isolate N-[4-(N,N-dimethylamino)-cyclohexyl]-4-(1-methyl-1,2,3,4-tetrazol-5-yl)thiobutyramide (yield: 47%). cooling the mixture is further stirred at room temperature for 2 hours After distilling off the solvent under reduced pressure the resulting residue is extracted with chloroform The chloroform layer is washed with 5% aqueous hydrochloric acid an aqueous saturated sodium hydrogen carbonate solution and an aqueous saturated sodium chloride solution and then dried over anhydrous sodium sulfate Chloroform is distilled off the resulting residue is subjected to silica gel column chromatography (Wakogel C-200, eluting solvent, benzene:chloroform=4:1, V/V)