1-(2-hydroxyethyl)-2,2,6,6-tetramethylpiperidin-4-ol

反応条件: temp:-20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Into a 250 ml flask equipped with a magnetic stirbar, thermometer, addition funnel and nitrogen atmosphere was placed 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-piperidinol (10.0 g, 0.499 mole) and 75 ml of methylene chloride. The resulting slurry was cooled to -20° C. and the addition funnel wash charged with acetic anhydride (5.1 g, 0.496 mole) and 15 ml of methylene chloride. The anhydride was added dropwise to the diol slurry with no apparent reaction. The mixture was warmed to 15° C. at which temperature the solids began to dissolve. The mixture was stirred at ambient temperature for 2 hours. The mixture was poured into 80 ml of 10% sodium carbonate (aqueous) and stirred for 15 minutes at ambient temperature. The mixture was transferred to a separatory funnel and extracted with 100 ml of methyl t-butyl ether. The ether solution was dried with anhydrous magnesium sulfate and the solvent removed using aspirator and high vacuum systems. The product was a white solid melting at 56°-58° C. This material was used without further purification. Into a 250 ml flask equipped with a magnetic stirbar thermometer, addition funnel the addition funnel wash The mixture was warmed to 15° C. at which temperature the solids to dissolve stirred for 15 minutes at ambient temperature The mixture was transferred to a separatory funnel extracted with 100 ml of methyl t-butyl ether The ether solution was dried with anhydrous magnesium sulfate the solvent removed This material was used without further purification

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

実験手順: Accordingly, the invention relates to a process for the preparation of 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-piperidinol from triacetoneamine, which comprises reducing triacetoneamine in a manner known per se by catalytic hydrogenation in water or in a polar organic solvent or in a mixture thereof with water, to give 2,2,6,6-tetramethyl-4-piperidinol, adding a catalytic amount of an inorganic or organic acid to the solution of 2,2,6,6-tetramethyl-4-piperidinol as obtained or after concentrating the solution by distillation, without further purification and/or isolation of the intermediate, with the proviso that, if the solution of the intermediate is concentrated, the addition of acid is made before or after the distillation, and that the concentrated solution or melt may be diluted again with the same solvent or with another solvent, and subsequently reacting said solution or melt of 2,2,6,6-tetramethyl-4-piperidinol with ethylene oxide in a molar excess of 1-35% in the temperature range from 60°-170° C.

反応条件: temp:-20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Into a 250 ml flask equipped with a magnetic stirbar, thermometer, addition funnel and nitrogen atmosphere was placed 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-piperidinol (10.0 g, 0.499 mole) and 75 ml of methylene chloride. The resulting slurry was cooled to -20° C. and the addition funnel was charged with acetic anhydride (5.1 g, 0.496 mole) and 15 ml of methylene chloride. The anhydride was added dropwise to the diol slurry with no apparent reaction. The mixture was warmed to 15° C. at which temperature the solids began to dissolve. The mixture was stirred at ambient temperature for 2 hours. The mixture was poured into 80 ml of 10% sodium carbonate (aqueous) and stirred for 15 minutes at ambient temperature. The mixture was transferred to a separatory funnel and extracted with 100 ml of methyl t-butyl ether. The ether solution was dried with anhydrous magnesium sulfate and the solvent removed using aspirator and high vacuum systems. The product was a white solid melting at 56°-58° C. This material was used without further purification. Into a 250 ml flask equipped with a magnetic stirbar thermometer, addition funnel The mixture was warmed to 15° C. at which temperature the solids to dissolve stirred for 15 minutes at ambient temperature The mixture was transferred to a separatory funnel extracted with 100 ml of methyl t-butyl ether The ether solution was dried with anhydrous magnesium sulfate the solvent removed This material was used without further purification

反応条件: temp:-20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Into a 250 ml flask equipped with a magnetic stirbar, thermometer, addition funnel and nitrogen atmosphere was placed 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-piperidinol (10.0 g, 0.499 mole) and 75 ml of methylene chloride. The resulting slurry was cooled to -20° C. and the addition funnel was charged with acetic anhydride (5.1 g, 0.496 mole) and 15 ml of methylene chloride. The anhydride was added dropwise to the diol slurry with no apparent reaction. The mixture was warmed to 15° C. at which temperature the solids began to dissolve. The mixture was stirred at ambient temperature for 2 hours. The mixture was poured into 80 ml of 10% sodium carbonate (aqueous) and stirred for 15 minutes at ambient temperature. The mixture was transferred to a separatory funnel and extracted with 100 ml of methyl t-butyl ether. The ether solution was dried with anhydrous magnesium sulfate and the solvent removed using aspirator and high vacuum systems. The product was a white solid melting at 56°-58° C. This material was used without further purification. Into a 250 ml flask equipped with a magnetic stirbar thermometer, addition funnel The mixture was warmed to 15° C. at which temperature the solids to dissolve stirred for 15 minutes at ambient temperature The mixture was transferred to a separatory funnel extracted with 100 ml of methyl t-butyl ether The ether solution was dried with anhydrous magnesium sulfate the solvent removed This material was used without further purification

反応条件: temp:-20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Into a 250 ml flask equipped with a magnetic stirbar, thermometer, addition funnel and nitrogen atmosphere was placed 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-piperidinol (10.0 g, 0.499 mole) and 75 ml of methylene chloride. The resulting slurry was cooled to -20° C. and the addition funnel was charged with acetic anhydride (5.1 g, 0.496 mole) and 15 ml of methylene chloride. The anhydride was added dropwise to the diol slurry with no apparent reaction. The mixture was warmed to 15° C. at which temperature the solids began to dissolve. The mixture was stirred at ambient temperature for 2 hours. The mixture was poured into 80 ml of 10% sodium carbonate (aqueous) and stirred for 15 minutes at ambient temperature. The mixture was transferred to a separatory funnel and extracted with 100 ml of methyl t-butyl ether. The ether solution was dried with anhydrous magnesium sulfate and the solvent removed using aspirator and high vacuum systems. The product was a white solid melting at 56°-58° C. This material was used without further purification. Into a 250 ml flask equipped with a magnetic stirbar thermometer, addition funnel The mixture was warmed to 15° C. at which temperature the solids to dissolve stirred for 15 minutes at ambient temperature The mixture was transferred to a separatory funnel extracted with 100 ml of methyl t-butyl ether The ether solution was dried with anhydrous magnesium sulfate the solvent removed This material was used without further purification

反応条件: temp:-20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Into a 250 ml flask equipped with a magnetic stirbar, thermometer, addition funnel and nitrogen atmosphere was placed 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-piperidinol (10.0 g, 0.499 mole) and 75 ml of methylene chloride. The resulting slurry was cooled to -20° C. and the addition funnel wash charged with acetic anhydride (5.1 g, 0.496 mole) and 15 ml of methylene chloride. The anhydride was added dropwise to the diol slurry with no apparent reaction. The mixture was warmed to 15° C. at which temperature the solids began to dissolve. The mixture was stirred at ambient temperature for 2 hours. The mixture was poured into 80 ml of 10% sodium carbonate (aqueous) and stirred for 15 minutes at ambient temperature. The mixture was transferred to a separatory funnel and extracted with 100 ml of methyl t-butyl ether. The ether solution was dried with anhydrous magnesium sulfate and the solvent removed using aspirator and high vacuum systems. The product was a white solid melting at 56°-58° C. This material was used without further purification. Into a 250 ml flask equipped with a magnetic stirbar thermometer, addition funnel the addition funnel wash The mixture was warmed to 15° C. at which temperature the solids to dissolve stirred for 15 minutes at ambient temperature The mixture was transferred to a separatory funnel extracted with 100 ml of methyl t-butyl ether The ether solution was dried with anhydrous magnesium sulfate the solvent removed This material was used without further purification

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

実験手順: Accordingly, the invention relates to a process for the preparation of 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-piperidinol from triacetoneamine, which comprises reducing triacetoneamine in a manner known per se by catalytic hydrogenation in water or in a polar organic solvent or in a mixture thereof with water, to give 2,2,6,6-tetramethyl-4-piperidinol, adding a catalytic amount of an inorganic or organic acid to the solution of 2,2,6,6-tetramethyl-4-piperidinol as obtained or after concentrating the solution by distillation, without further purification and/or isolation of the intermediate, with the proviso that, if the solution of the intermediate is concentrated, the addition of acid is made before or after the distillation, and that the concentrated solution or melt may be diluted again with the same solvent or with another solvent, and subsequently reacting said solution or melt of 2,2,6,6-tetramethyl-4-piperidinol with ethylene oxide in a molar excess of 1-35% in the temperature range from 60°-170° C.

反応条件: temp:-20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Into a 250 ml flask equipped with a magnetic stirbar, thermometer, addition funnel and nitrogen atmosphere was placed 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-piperidinol (10.0 g, 0.499 mole) and 75 ml of methylene chloride. The resulting slurry was cooled to -20° C. and the addition funnel was charged with acetic anhydride (5.1 g, 0.496 mole) and 15 ml of methylene chloride. The anhydride was added dropwise to the diol slurry with no apparent reaction. The mixture was warmed to 15° C. at which temperature the solids began to dissolve. The mixture was stirred at ambient temperature for 2 hours. The mixture was poured into 80 ml of 10% sodium carbonate (aqueous) and stirred for 15 minutes at ambient temperature. The mixture was transferred to a separatory funnel and extracted with 100 ml of methyl t-butyl ether. The ether solution was dried with anhydrous magnesium sulfate and the solvent removed using aspirator and high vacuum systems. The product was a white solid melting at 56°-58° C. This material was used without further purification. Into a 250 ml flask equipped with a magnetic stirbar thermometer, addition funnel The mixture was warmed to 15° C. at which temperature the solids to dissolve stirred for 15 minutes at ambient temperature The mixture was transferred to a separatory funnel extracted with 100 ml of methyl t-butyl ether The ether solution was dried with anhydrous magnesium sulfate the solvent removed This material was used without further purification