1-(4-chlorobutyl)piperidine

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

実験手順: A solution of 13.1 g (0.075 mole) of 4-piperidinobutyl chloride in 100 ml of toluene is added to a mixture of 4.9 g (0.025 mole) of 2,7-dihydroxyfluorene and 2.7 g (0.05 mole) of sodium methoxide in 200 ml of toluene. The mixture is refluxed with stirring for 12 hours. Upon cooling, the mixture is filtered to remove the precipitated sodium chloride. The toluene solution is washed with water, then with sodium chloride solution and dried over anhydrous magnesium sulfate. This mixture is filtered and the filtrate acidified to Congo Red with ethereal HCl. The precipitate is collected and recrystallized from butanone-methanol to give 2,7-bis(4-piperidinobutoxy)fluorene dihydrochloride. The mixture is refluxed Upon cooling the mixture is filtered to remove the precipitated sodium chloride The toluene solution is washed with water with sodium chloride solution and dried over anhydrous magnesium sulfate This mixture is filtered The precipitate is collected recrystallized from butanone-methanol

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

実験手順: In a 2 L three-necked round bottomed flask was added piperidine (85.15 g, 1.0 mol) acetone (1000 mL), and anhydrous potassium carbonate (276.42 g, 2.0 mol, 2.0 equiv.). The flask was equipped with a mechanical stirrer and a condenser. 4-chloro-1-bromo-butane (188.6 g, 1.1 mol, 1.1 equiv.) was added dropwise under continuous stirring at room temperature over a period of 30 min. The suspension mixture was then stirred at 40° C. The progress of the reaction was monitored by TLC, which confirmed the reaction was completed after 4 hours. The mixture was cooled to room temperature and the insoluble materials were removed by filtration and washed with dichloromethane (2×100 mL). The combined filtrates were concentrated under vacuum until it became dry. The residue was then mixed with dichloromethane (500 mL). Insoluble materials were removed by filtration and washed by dichloromethane (2×100 mL). The combined filtrate and washings were concentrated and purified through a flash silica gel column, which gave the expected product as light yellow oil (98.39 g, 56% yield). The flask was equipped with a mechanical stirrer and a condenser The suspension mixture was then stirred at 40° C was completed after 4 hours The mixture was cooled to room temperature the insoluble materials were removed by filtration washed with dichloromethane (2×100 mL) The combined filtrates were concentrated under vacuum until it became dry The residue was then mixed with dichloromethane (500 mL) Insoluble materials were removed by filtration washed by dichloromethane (2×100 mL) The combined filtrate and washings were concentrated purified through a flash silica gel column, which

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

実験手順: In a 2 L three-necked round bottomed flask was added piperidine (85.15 g, 1.0 mol) acetone (1000 mL), and anhydrous potassium carbonate (276.42 g, 2.0 mol, 2.0 equiv.). The flask was equipped with a mechanical stirrer and a condenser. 4-chloro-1-bromo-butane (188.6 g, 1.1 mol, 1.1 equiv.) was added dropwise under continuous stirring at room temperature over a period of 30 min. The suspension mixture was then stirred at 40° C. The progress of the reaction was monitored by TLC, which confirmed the reaction was completed after 4 hours. The mixture was cooled to room temperature and the insoluble materials were removed by filtration and washed with dichloromethane (2×100 mL). The combined filtrates were concentrated under vacuum until it became dry. The residue was then mixed with dichloromethane (500 mL). Insoluble materials were removed by filtration and washed by dichloromethane (2×100 mL). The combined filtrate and washings were concentrated and purified through a flash silica gel column, which gave the expected product as light yellow oil (98.39 g, 56% yield). The flask was equipped with a mechanical stirrer and a condenser The suspension mixture was then stirred at 40° C was completed after 4 hours The mixture was cooled to room temperature the insoluble materials were removed by filtration washed with dichloromethane (2×100 mL) The combined filtrates were concentrated under vacuum until it became dry The residue was then mixed with dichloromethane (500 mL) Insoluble materials were removed by filtration washed by dichloromethane (2×100 mL) The combined filtrate and washings were concentrated purified through a flash silica gel column, which

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

実験手順: A solution of 13.1 g (0.075 mole) of 4-piperidinobutyl chloride in 100 ml of toluene is added to a mixture of 4.9 g (0.025 mole) of 2,7-dihydroxyfluorene and 2.7 g (0.05 mole) of sodium methoxide in 200 ml of toluene. The mixture is refluxed with stirring for 12 hours. Upon cooling, the mixture is filtered to remove the precipitated sodium chloride. The toluene solution is washed with water, then with sodium chloride solution and dried over anhydrous magnesium sulfate. This mixture is filtered and the filtrate acidified to Congo Red with ethereal HCl. Teh precipitate is collected and recrystallized from butanonemethanol to give 2,7-bis(4-piperidinobutoxy)fluorene dihydrochloride. The mixture is refluxed Upon cooling the mixture is filtered to remove the precipitated sodium chloride The toluene solution is washed with water with sodium chloride solution and dried over anhydrous magnesium sulfate This mixture is filtered Teh precipitate is collected recrystallized from butanonemethanol

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

実験手順: A solution of 13.1 g (0.075 mole) of 4-piperidinobutyl chloride in 100 ml of toluene is added to a mixture of 4.9 g (0.025 mole) of 2,7-dihydroxyfluorene and 2.7 g (0.05 mole) of sodium methoxide in 200 ml of toluene. The mixture is refluxed with stirring for 12 hours. Upon cooling, the mixture is filtered to remove the precipitated sodium chloride. The toluene solution is washed with water, then with sodium chloride solution and dried over anhydrous magnesium sulfate. This mixture is filtered and the filtrate acidified to Congo Red with ethereal HCl. The precipitate is collected and recrystallized from butanone-methanol to give 2,7-bis(4-piperidinobutoxy)fluorene dihydrochloride. The mixture is refluxed Upon cooling the mixture is filtered to remove the precipitated sodium chloride The toluene solution is washed with water with sodium chloride solution and dried over anhydrous magnesium sulfate This mixture is filtered The precipitate is collected recrystallized from butanone-methanol