heptan-4-one

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: Added to a suspension of 1 g of 2-bromo-4-fluorophenethylamine hydrocloride in 25 cm3 of dichloromethane and under an inert atmosphere is 663 μL of triethylamine. After stirring for 30 min at a temperature close to 20° C., 5 cm3 of distilled water are added and the stirring is continued for 30 min. 15 cm3 of distilled water are added and the two phases are separated. The organic phase is washed with three lots of 10 cm3 of distilled water, then dried. Added to the solution obtained are successively 449 mg of 4-heptanone and 1.166 g of sodium triacetoxyborohydride. The reaction mixture is stirred for 15 h at a temperature close to 20° C. 20 cm3 of a saturated solution of sodium hydrogen carbonate are then added to the reaction medium. The organic phase is decanted and separated from the aqueous phase then washed successively with 15 cm3 of distilled water and 15 cm3 of a saturated solution of sodium chloride. The organic phase is dried then concentrated using a rotary evaporator under reduced pressure (5 kPa). 1.069 g of N-[2-(2-bromo-4-fluorophenyl)ethyl]heptan-4-amine are obtained in the form of a colorless oil. close to 20° C. the stirring is continued for 30 min the two phases are separated The organic phase is washed with three lots of 10 cm3 of distilled water dried Added to the solution obtained The reaction mixture is stirred for 15 h at a temperature close to 20° C The organic phase is decanted separated from the aqueous phase then washed successively with 15 cm3 of distilled water and 15 cm3 of a saturated solution of sodium chloride The organic phase is dried then concentrated a rotary evaporator under reduced pressure (5 kPa)

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

実験手順: Added to a suspension of 1 g of 2-bromo-4-trifluoromethylphenethylamine hydrocloride in 25 cm3 of dichloroethane and under an inert atmosphere is 0.5 cm3 of triethylamine. After stirring for 30 min at a temperature close to 20° C., 5 cm3 of distilled water are added and the stirring is continued for 30 min. The two phases are separated and the organic phase is dried. Added to the solution obtained are successively 375 mg of 4-heptanone and 970 mg of sodium triacetoxyborohydride. The reaction mixture is stirred for 15 h at a temperature close to 20° C. 20 cm3 of a saturated solution of sodium hydrogen carbonate are then added to the reaction medium. The organic phase is decanted and separated from the aqueous phase then washed successively with 15 cm3 of distilled water and 15 cm3 of a saturated solution of sodium chloride. The organic phase is dried then concentrated using a rotary evaporator under reduced pressure (5 kPa). 1.16 g of N-[2-(2-bromo-4-trifluoromethylphenyl)ethyl]heptan-4-amine are obtained in the form of a colorless oil. close to 20° C. the stirring is continued for 30 min The two phases are separated the organic phase is dried Added to the solution obtained The reaction mixture is stirred for 15 h at a temperature close to 20° C The organic phase is decanted separated from the aqueous phase then washed successively with 15 cm3 of distilled water and 15 cm3 of a saturated solution of sodium chloride The organic phase is dried then concentrated a rotary evaporator under reduced pressure (5 kPa)

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

実験手順: 10 g of 2-bromophenethylamine and 5.71 g of 4-heptanone are dissolved in 250 cm3 of 1,2-dichloroethane at a temperature close to 20° C. 14.84 g of sodium triacetoxyborohydride and 2.9 cm3 of glacial acetic acid are added to the reaction medium. Stirring is continued for 20 h. 300 cm3 of 1M sodium hydroxide are added to the reaction medium. The aqueous phase is extracted with 3 lots of 100 cm3 of ethyl acetate. The organic phases are combined and washed with 4 lots of 100 cm3 of water then 100 cm3 of a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, and concentrated using a rotary evaporator under reduced pressure (5 kPa). The yellow liquid obtained is purified by flash chromatography over silica (column: 400 g; particle size: 20-40 μm, spherical; flow rate: 30 cm3/min; eluent: 100% heptane to 70% ethyl acetate/30% heptane gradient). After concentrating the fractions under reduced pressure, 17.33 g of N-[2-(2-bromophenyl)ethyl]heptan-4-amine are obtained. close to 20° C The aqueous phase is extracted with 3 lots of 100 cm3 of ethyl acetate washed with 4 lots of 100 cm3 of water 100 cm3 of a saturated aqueous solution of sodium chloride, dried over magnesium sulfate concentrated a rotary evaporator under reduced pressure (5 kPa) The yellow liquid obtained is purified by flash chromatography over silica (column: 400 g; particle size: 20-40 μm, spherical; flow rate: 30 cm3/min; eluent: 100% heptane to 70% ethyl acetate/30% heptane gradient) After concentrating the fractions under reduced pressure, 17.33 g of N-[2-(2-bromophenyl)ethyl]heptan-4-amine are obtained

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

実験手順: Under the nitrogen gas atmosphere, a solution of 4-heptanone (5.0 mM, 35.75 mmol), n-butylamine (4.25 mL, 4.29 mmol), and three drops of concentrated hydrochloric acid was stirred for 18.5 hours at room temperature. After that, water was added and the mixture was extracted with ethyl acetate. After the organic layer had been washed with water and then dried with anhydrous sodium sulfate, the solvent was removed by distillation under reduced pressure. The obtained oily matter was dissolved in 2-methoxyethyl ether (40 mL), and heated and stirred with dimethyl methoxymethylenemalonate (5.66 g, 32.5 mmol) at 120° C. for 3 hours. After the solvent had been removed by distillation under reduced pressure, the residue was refined with silica gel (100 g) column chromatography (ethyl acetate-hexane of 1:1 in mixing ratio and then that of 2:1), and a ark reddish-brown oily substance was obtained. The substance was dissolved in THF (20 mL) without purification, and a 1M lithium hydroxide aqueous solution (15.18 mL) and water (4.82 mL) were added, and then the mixture was stirred for 2 hours at room temperature. After that, the mixture was diluted with water and washed with diethyl ether. After 2M hydrochloric acid had been added to the water layer to acidify it, the water layer was extracted with ethyl acetate. The organic layer was washed with water and then dried with anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure and a pale yellow solid (AA03, 1.68 g, 18%) was obtained. the mixture was extracted with ethyl acetate After the organic layer had been washed with water dried with anhydrous sodium sulfate the solvent was removed by distillation under reduced pressure The obtained oily matter was dissolved in 2-methoxyethyl ether (40 mL) heated After the solvent had been removed by distillation under reduced pressure in mixing ratio that of 2:1), and a ark reddish-brown oily substance was obtained washed with diethyl ether After 2M hydrochloric acid had been added to the water layer the water layer was extracted with ethyl acetate The organic layer was washed with water dried with anhydrous sodium sulfate The solvent was removed by distillation under reduced pressure a pale yellow solid (AA03, 1.68 g, 18%) was obtained