3-(4-hydroxyphenyl)propanamide

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: 25% Aqueous ammonia (30 mL) was added to methyl 4-hydroxybenzenepropanoate (1.5 g, 8.3 mmol), and the mixture was stirred at room temperature for 15 hrs. Dil. hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give the title compound (0.43 g, yield 31%). the mixture was extracted with ethyl acetate The extract was washed with water concentrated under reduced pressure The residue was recrystallized from ethyl acetate-hexane

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

実験手順: 25% Aqueous ammonia (30 mL) was added to methyl 4-hydroxybenzenepropanoate (1.5 g, 8.3 mmol), and the mixture was stirred at room temperature for 15 hrs. Dil. hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give the title compound (0.43 g, yield 31%). the mixture was extracted with ethyl acetate The extract was washed with water concentrated under reduced pressure The residue was recrystallized from ethyl acetate-hexane

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

実験手順: A mixture of 106 mg (0.64 mmol) 3-(4-hydroxy-phenyl)-propionamide, 178 mg (1.29 mmol) potassium carbonate and 140 mg (0.68 mmol) 3,4-difluorobenzyl bromide in 5 ml ethyl methyl ketone is hold at 50° C. for 24 hours. The reaction mixture is cooled, diluted with water and extracted with diethyl ether. Crystallization from n-hexane yields 77 mg (41%) of a colorless solid. MS: m/e=291.3 (M+). The reaction mixture is cooled extracted with diethyl ether Crystallization from n-hexane

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

実験手順: N,N′-dicyclohexylcarbodiimide (2.48 g, 0.012 mol) was added to chilled (0° C.) 3-(4-hydroxyphenyl)propanoic acid solution (2 g, 0.012 mol) and 4-nitrophenol (1.95 g, 0.014 mol) in ethyl acetate (25 cm3) and mixed magnetically at 0° C. for 30 min. The reaction mixture was then stirred magnetically for 2 h at room temperature. Thereafter, the precipitated N,N′-dicyclohexylureaa was filtered out, washed using ethyl acetate (5 cm3) and the combined filtrates were evaporated until dry. Anhydrous methanol saturated with ammonia (10 cm3) was added and the reaction mixture was stirred magnetically for 2 hrs, thereafter the mixture was evaporated until dry, and the remainder was loaded onto a chromatography column packed with Merck 60H silica gel (5-40 μm). The column was eluted with chloroform-methanol (50:1, v/v). The chromatographically purified product was crystallized out of the methanol and then vacuum desiccated over phosphorus pentocide yielding 1.45 g 3-(4-hydroxyphenyl)propanoic acid amide (75% efficiency) (FIG. 1). mixed magnetically at 0° C. for 30 min Thereafter, the precipitated N,N′-dicyclohexylureaa was filtered out washed the combined filtrates were evaporated until dry Anhydrous methanol saturated with ammonia (10 cm3) was added the reaction mixture was stirred magnetically for 2 hrs the mixture was evaporated until dry The column was eluted with chloroform-methanol (50:1 The chromatographically purified product was crystallized out of the methanol

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

実験手順: Preferentially, when in that in the manufacture of anti-aging compositions the synthesis of 3-(4-hydroxyphenyl)propanoic acid amide 0.5-5 g of 3-(4-hydroxyphenyl)propanoic acid solution are used, with 0.5-5 g 4-nitrophenol in ethyl oxide, 5-15 times excess N,N′-dicyclohexylcarbodiimide in relation to 4-nitrophenol, and the anhydrous methanol saturated with ammonia is between 5-30 cm3, wherein the reaction mixture is mixed in a temperature range of 0-10° C. for 10-50 min, whereafter it is mixed at room temperature for 1.5-3 h, then the precipitated N,N′-dicyclohexylurea is filtered out and washed in 2-15 cm3 ethyl acetate. The next subject of the present invention is an anti-aging composition, characterized in that it contains 3-(4-hydroxyphenyl)propanoic acid amide at a concentration between 1 and 500 μmol. Preferentially, the composition contains 3-(4-hydroxyphenyl)propanoic acid amide, obtained through the synthesis of 3-(4-hydroxyphenyl)propanoic acid amide is performed using active 4-nitrophenyl ester where the concentration of 3-4-hydroxyphenyl)propanoic acid is 0.12-0.0012 mol, where the reaction is performed with ammonia at room temperature, and the 4-nitrophenol in ethyl acetate is supplemented with N,N′-dicyclohexylocarbodiimide, then the reaction mixture is stirred, the N,N′-dicyclohexylurea precipitate is then filtered out and dried under vacuum, the remainder is supplemented with anhydrous methanol saturated with ammonia (10 cm3) and the reaction mixture is stirred and evaporated until dry, then the remainder is loaded onto a silica gel chromatography column, and the latter is washed with chloroform-metanol (50:1, v/v), whence the chromatographically clean product is crystallized from methanol and then dried in a vacuum dessicator over phosphorus pentoxide yielding 3-(4-hydroxyphenyl)propanoic acid amide. Preferentially, 0.5-5 g of 3-(4-hydroxyphenyl)propanoic acid solution are used, with 0.5-5 g 4-nitrophenol in ethyl oxide, 5-15 times excess N,N′-dicyclohexylcarbodiimide in relation to 4-nitrophenol, and the anhydrous methanol saturated with ammonia is between 5-30 cm3, wherein the reaction mixture is mixed in a temperature range of 0-10° C. for 10-50 min, whereafter it is mixed at room temperature for 1.5-3 h, then the precipitated N,N′-dicyclohexylurea is filtered out and washed in 2-15 cm3 ethyl acetate. Preferentially, the composition is applicable in the cosmetics and/or pharmaceutical industries. the N,N′-dicyclohexylurea precipitate is then filtered out dried under vacuum the reaction mixture is stirred evaporated until dry the latter is washed with chloroform-metanol (50:1 v/v), whence the chromatographically clean product is crystallized from methanol dried in a vacuum dessicator over phosphorus pentoxide