ethyl 4-(cyanomethyl)benzoate

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 solution of 10 g (53 mol) of ethyl 4-cyanomethyl-benzoate and 2.02 mL of a 1 M sodium hydroxide solution in 100 mL of ethanol is refluxed for one hour. Then the reaction solution is evaporated down and the residue is combined with ice water. Concentrated hydrochloric acid is added dropwise to the reaction solution until no more precipitate is formed. The precipitate is filtered off, washed twice with water and dried. Then the reaction solution is evaporated down Concentrated hydrochloric acid is added dropwise to the reaction solution until no more precipitate is formed The precipitate is filtered off washed twice with water dried

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

実験手順: A solution of 10 g (53 mol) of ethyl 4-cyanomethyl-benzoate and 2.02 mL of a 1 M sodium hydroxide solution in 100 mL of ethanol is refluxed for one hour. Then the reaction solution is evaporated down and the residue is combined with ice water. Concentrated hydrochloric acid is added dropwise to the reaction solution until no more precipitate is formed. The precipitate is filtered off, washed twice with water and dried. Then the reaction solution is evaporated down Concentrated hydrochloric acid is added dropwise to the reaction solution until no more precipitate is formed The precipitate is filtered off washed twice with water dried

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

実験手順: Prepared analogously to Example 64 from 1-(2-piperidinophenyl)-1-butanol and ethyl 4-cyanomethyl-benzoate with concentrated sulfuric acid in o-dichlorobenzene at ambient temperature.

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

実験手順: Prepared analogously to Example 64 from 1-(2-piperidinophenyl)-1-butanol and ethyl 4-cyanomethyl-benzoate with concentrated sulfuric acid in o-dichlorobenzene at ambient temperature.

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

実験手順: A mixture of 0.22 gm (0.8 m mol) of α-(3-methyl-phenyl)-2-piperidino-benzyl alcohol and 0.15 gm (0.8 m mol) of ethyl 4-cyanomethyl-benzoate in 2 ml of o-dichlorobenzene was added dropwise, at ambient temperature, to 1.5 ml of o-dichlorobenzene and 1.5 ml of concentrated sulfuric acid. After stirring for two hours, the mixture was poured onto ice water, extracted once with ether, made alkaline with dilute sodium hydroxide solution, and extracted with chloroform. The chloroform extract was concentrated by evaporation, and the residue was recrystallized from ethanol. the mixture was poured onto ice water extracted once with ether extracted with chloroform The chloroform extract was concentrated by evaporation the residue was recrystallized from ethanol

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

実験手順: A mixture of 0.22 gm (0.8 m mol) of α-(3-methyl-phenyl)-2-piperidino-benzyl alcohol and 0.15 gm (0.8 m mol) of ethyl 4-cyanomethyl-benzoate in 2 ml of o-dichlorobenzene was added dropwise, at ambient temperature, to 1.5 ml of o-dichlorobenzene and 1.5 ml of concentrated sulfuric acid. After stirring for two hours, the mixture was poured onto ice water, extracted once with ether, made alkaline with dilute sodium hydroxide solution, and extracted with chloroform. The chloroform extract was concentrated by evaporation, and the residue was recrystallized from ethanol. the mixture was poured onto ice water extracted once with ether extracted with chloroform The chloroform extract was concentrated by evaporation the residue was recrystallized from ethanol

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: An amount of 1.6 ml of conc. sulfuric acid was added in small drops to a mixture of 2 gm (9.74 m mol) of 1-(2-piperidino-phenyl)-ethanol and 4 gm (21.1 m mol) of 4-cyanomethylbenzoic acid ethyl ester under stirring and cooling with ice by keeping the internal temperature at 35° to 40° C. Subsequently, the mixture was heated for 2.5 hours in a bath of 80° C., a further 2 gm (10.5 m mol) of 4-cyanomethyl benzoic acid ethyl ester and 0.8 ml of conc. sulfuric acid were added, and heating was continued for one hour at 80° C. and for three hours at 100° C. After that time no starting alcohol could be detected in a thin layer chromatogram. After cooling to 20° C. the mixture was layered with ethyl acetate, and under stirring and cooling ice water was added. After extraction several times with ethyl acetate, the organic extract was dried over sodium sulfate, filtered, and evaporated in vacuo. The evaporation residue was purified by column chromatography on silica gel (toluene/acetone=10:1). From the pre-fractions 0.5 gm of 2-piperidino-styrol was isolated. cooling with ice at 35° to 40° C heating After cooling to 20° C. the mixture under stirring was added After extraction several times with ethyl acetate the organic extract was dried over sodium sulfate filtered evaporated in vacuo The evaporation residue was purified by column chromatography on silica gel (toluene/acetone=10:1)

反応条件: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Ethyl 4-cyanomethylbenzoate (approximately 8 g) was dissolved in DME (10 ml). The solution was added tris(n-butyl)tin azide (5 ml) and the resultant solution was stirred and heated at 85° C. overnight. The solution was cooled to room temperature. The cooled solution was diluted with methanol then acidified with 1N hydrochloric acid. The acidified mixture was stirred for one hour then partitioned between ethyl acetate and water. The organic layer was separated, dried over magnesium sulfate, filtered, and concentrated in vacuo. The solution was cooled to room temperature then partitioned between ethyl acetate and water The organic layer was separated dried over magnesium sulfate filtered concentrated in vacuo

反応条件: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Ethyl 4-cyanomethylbenzoate (approximately 8 g) was dissolved in DME (10 ml). The solution was added tris(n-butyl)tin azide (5 ml) and the resultant solution was stirred and heated at 85° C. overnight. The solution was cooled to room temperature. The cooled solution was diluted with methanol then acidified with 1N hydrochloric acid. The acidified mixture was stirred for one hour then partitioned between ethyl acetate and water. The organic layer was separated, dried over magnesium sulfate, filtered, and concentrated in vacuo. The solution was cooled to room temperature then partitioned between ethyl acetate and water The organic layer was separated dried over magnesium sulfate filtered concentrated in vacuo

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

実験手順: A solution of 10 g (53 mol) of ethyl 4-cyanomethyl-benzoate and 2.02 mL of a 1 M sodium hydroxide solution in 100 mL of ethanol is refluxed for one hour. Then the reaction solution is evaporated down and the residue is combined with ice water. Concentrated hydrochloric acid is added dropwise to the reaction solution until no more precipitate is formed. The precipitate is filtered off, washed twice with water and dried. Then the reaction solution is evaporated down Concentrated hydrochloric acid is added dropwise to the reaction solution until no more precipitate is formed The precipitate is filtered off washed twice with water dried

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

実験手順: Prepared analogously to Example 64 from 1-(2-piperidinophenyl)-1-butanol and ethyl 4-cyanomethyl-benzoate with concentrated sulfuric acid in o-dichlorobenzene at ambient temperature.