2-piperidin-4-ylacetonitrile

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: Add trifluoroacetic acid (23 mL, 34.7 g, 304 mmol) to 4-cyanomethylpiperidine-1-carboxylic acid t-butyl ester (5.43 g, 24.21 mmol) in DCM (25 mL) and stir at room temperature for 18 hr. Remove the solvent in vacuo and dissolve in methanol (50 mL) and pour onto an SCX-2 column. Elute with 2 M ammonia in methanol and evaporate the eluent to give piperidin-4-ylacetonitrile as an oil which solidifies on standing (2.78 g, 92%). MS (m/z): 125.1 (M+1). Remove the solvent in vacuo dissolve in methanol (50 mL) pour onto an SCX-2 column Elute with 2 M ammonia in methanol evaporate the eluent

反応条件: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of crude trifluoromethanesulfonic acid 1-(4-methoxy-2,6-dimethylphenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl ester (1.1 g), N,N-diisopropylethylamine (0.65 g) and piperidin-4-yl-acetonitrile (1.6 g) was heated at 150° C. in a sealed tube for 7 hours. After cooling to room temperature, ethyl acetate and water were poured into the mixture, and separated. The aqueous phase was extracted with ethyl acetate, and the organic phase was dried over MgSO4 and filtered. The filtrate was concentrated under reduced pressure and the residue was purified with column chromatography (silica gel: Wako gel C200, eluent: hexane:ethyl acetate=3/1) to obtain {1-[1-(4-methoxy-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-acetonitrile (0.58 g) as a pale yellow crystal. After cooling to room temperature separated The aqueous phase was extracted with ethyl acetate the organic phase was dried over MgSO4 filtered The filtrate was concentrated under reduced pressure the residue was purified with column chromatography (silica gel: Wako gel C200, eluent: hexane:ethyl acetate=3/1)

反応条件: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of crude trifluoromethanesulfonic acid 1-(4-methoxy-2,6-dimethylphenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl ester (1.1 g), N,N-diisopropylethylamine (0.65 g) and piperidin-4-yl-acetonitrile (1.6 g) was heated at 150° C. in a sealed tube for 7 hours. After cooling to room temperature, ethyl acetate and water were poured into the mixture, and separated. The aqueous phase was extracted with ethyl acetate, and the organic phase was dried over MgSO4 and filtered. The filtrate was concentrated under reduced pressure and the residue was purified with column chromatography (silica gel: Wako gel C200, eluent: hexane:ethyl acetate=3/1) to obtain {1-[1-(4-methoxy-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-acetonitrile (0.58 g) as a pale yellow crystal. After cooling to room temperature separated The aqueous phase was extracted with ethyl acetate the organic phase was dried over MgSO4 filtered The filtrate was concentrated under reduced pressure the residue was purified with column chromatography (silica gel: Wako gel C200, eluent: hexane:ethyl acetate=3/1)

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: Add trifluoroacetic acid (23 mL, 34.7 g, 304 mmol) to 4-cyanomethylpiperidine-1-carboxylic acid t-butyl ester (5.43 g, 24.21 mmol) in DCM (25 mL) and stir at room temperature for 18 hr. Remove the solvent in vacuo and dissolve in methanol (50 mL) and pour onto an SCX-2 column. Elute with 2 M ammonia in methanol and evaporate the eluent to give piperidin-4-ylacetonitrile as an oil which solidifies on standing (2.78 g, 92%). MS (m/z): 125.1 (M+1). Remove the solvent in vacuo dissolve in methanol (50 mL) pour onto an SCX-2 column Elute with 2 M ammonia in methanol evaporate the eluent

反応条件: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of crude trifluoromethanesulfonic acid 1-(4-methoxy-2,6-dimethylphenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl ester (1.1 g), N,N-diisopropylethylamine (0.65 g) and piperidin-4-yl-acetonitrile (1.6 g) was heated at 150° C. in a sealed tube for 7 hours. After cooling to room temperature, ethyl acetate and water were poured into the mixture, and separated. The aqueous phase was extracted with ethyl acetate, and the organic phase was dried over MgSO4 and filtered. The filtrate was concentrated under reduced pressure and the residue was purified with column chromatography (silica gel: Wako gel C200, eluent: hexane:ethyl acetate=3/1) to obtain {1-[1-(4-methoxy-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-acetonitrile (0.58 g) as a pale yellow crystal. After cooling to room temperature separated The aqueous phase was extracted with ethyl acetate the organic phase was dried over MgSO4 filtered The filtrate was concentrated under reduced pressure the residue was purified with column chromatography (silica gel: Wako gel C200, eluent: hexane:ethyl acetate=3/1)