N-butyl-2,2,6,6-tetramethylpiperidin-4-amine

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2.36 g of ethyl N-(2,4-dichloro-1,3,5-triazin-6-yl)glycinate [obtained as described in Preparation 4(A)], 4.19 g of 2,2,6,6-tetramethyl-4-(butylamino)piperidine [obtained as described in Preparation i(A)] and 2.77 g of sodium bicarbonate were heated under reflux in 20 ml of xylene for 29 hours. At the end of this time, the xylene was removed by distillation under reduced pressure, and a mixture of methylene chloride and water was added to the resulting residue, after which the mixture was shaken. The methylene chloride layer was separated, dried and concentrated by evaporation under reduced pressure, and the resulting residue was purified by silica gel column chromatography (using a 20:10:1:1 by volume mixture of hexane, diethyl ether, ethanol and triethylamine as eluent), to yield 5.46 g of the title compound melting at 40° C. At the end of this time, the xylene was removed by distillation under reduced pressure a mixture of methylene chloride and water was added to the resulting residue The methylene chloride layer was separated dried concentrated by evaporation under reduced pressure the resulting residue was purified by silica gel column chromatography ( by volume mixture of hexane, diethyl ether, ethanol and triethylamine as eluent),

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 155 g of 2,2,6,6-tetramethyl-4-piperidone and 80.0 g of butylamine were dissolved in 300 ml of methanol, and then 2.0 g of platinum oxide were added to the resulting solution, after which the solution was shaken under a pressure of 3 atmospheres of hydrogen in a medium-pressure hydrogenation apparatus at room temperature for 5 hours. At the end of this time, the platinum catalyst was filtered off, and the solvent was removed from the filtrate by distillation under reduced pressure, after which the residue was further purified by distillation under reduced pressure, to yield 201.5 g of the title compound as an oil boiling at 100° to 101° C./5 mmHg (667 Pa). At the end of this time, the platinum catalyst was filtered off the solvent was removed from the filtrate by distillation under reduced pressure after which the residue was further purified by distillation under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The N-butyl-N-ethoxycarbonyl-2,2,6,6-tetramethyl-4-piperidylamine is prepared by reacting N-butyl-2,2,6,6-tetramethyl-4-piperidylamine with ethyl chlorocarbonate at 15°-25° C. in toluene in the presence of an aqueous solution of K2CO3. The product obtained, which is 99.2% pure, is employed directly, without any purification. at 15°-25° C. The product obtained is employed directly, without any purification

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: If 1,3-bis(2-chloro-5-ethyl-1,3,2-dioxaphosphorinan-5-yl)-2-oxapropane is reacted with 4-butylamino-2,2,6,6-tetramethylpiperidine in a procedure analogous to Example 2, 1,3-bis[2-(N-butyl-N-(2,2,6,6-tetramethyl-4-piperidyl)amino)-5-ethyl-1,3,2-dioxaphosphorinan-5-yl]-2-oxapropane is obtained as a viscous resin (Compound No. 22, formula below, R3 =H); FD-MS: 730 (M+).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under agitation, 392.9 g (1.85 moles) of 4-n-butylamino-2,2,6,6-tetramethylpiperidine, 10.0 g (0.0877 mole) of quadratic acid, and 150 cc of 2-ethylhexanol were heated to boiling under reflux in a 1-liter agitated flask with water trap; s temperature rose from 205° to 217° C., and 2.8 cc of water was removed from the cycle. The reaction solution was then distilled. The residue was boiled with petroleum ether. After cooling, vacuum-filtering, and drying, 38.9 g was obtained (88.2% yield), mp 151°-152° C. Extinction (g/l.cm) at 278 nm: 25; at 335 nm: 83. under reflux in a 1-liter rose from 205° to 217° C. 2.8 cc of water was removed from the cycle The reaction solution was then distilled After cooling vacuum-filtering drying 38.9 g was obtained (88.2% yield), mp 151°-152° C

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 18.4 g of cyanuric chloride in 200 ml of dioxane was added dropwise, with stirring, a solution of 43.6 g of 4-butylamino-2,2,6,6-tetramethylpiperidine in 100 ml of dioxane at 20°-25° C. The mixture was stirred at the same temperature for 2 hours, after which it was stirred at 60°-70° C. for 2 hours. At the end of this time, the dioxane was distilled off and the residue was poured into a 10% aqueous solution of potassium carbonate and extracted with ethyl acetate. The extract was dried over anhydrous potassium carbonate, and then the ethyl acetate was distilled off. The resulting oil was purified by column chromatography through silica gel, eluted with a 20:1:1 by volume mixture of ethyl acetate, ethanol and triethylamine, to give the title compound in the form of crystals melting at 40°-42° C. at 20°-25° C The mixture was stirred at the same temperature for 2 hours after which it was stirred at 60°-70° C. for 2 hours At the end of this time, the dioxane was distilled off the residue was poured into a 10% aqueous solution of potassium carbonate extracted with ethyl acetate The extract was dried over anhydrous potassium carbonate the ethyl acetate was distilled off The resulting oil was purified by column chromatography through silica gel eluted with a 20:1:1 by volume mixture of ethyl acetate, ethanol and triethylamine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2.0 g of platinum oxide were added to a solution of 155 g of 2,2,6,6-tetramethyl-4-piperidone and 80 g of butylamine in 300 ml of methanol. The resulting mixture was then hydrogenated under a hydrogen atmosphere in a Parr hydrogenation apparatus at room temperature for 5 hours. After completion of the reaction, the platinum catalyst was filtered off and the solvent was distilled from the filtrate under reduced pressure. The residue was purified by vacuum distillation, to give the desired product as an oil, boiling at 100°-101° C./5 mmHg (667 Pascals). After completion of the reaction the platinum catalyst was filtered off the solvent was distilled from the filtrate under reduced pressure The residue was purified by vacuum distillation

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2.0 g of platinum oxide were added to a solution of 155 g of 2,2,6,6-tetramethyl-4-piperidone and 80 g of butylamine in 300 ml of methanol. The resulting mixture was then hydrogenated under a hydrogen atmosphere in a Parr hydrogenation apparatus at room temperature for 5 hours. After completion of the reaction, the platinum catalyst was filtered off and the solvent was distilled from the filtrate under reduced pressure. The residue was purified by vacuum distillation, to give the desired product as an oil, boiling at 100°-101° C./5 mmHg (667 Pascals). After completion of the reaction the platinum catalyst was filtered off the solvent was distilled from the filtrate under reduced pressure The residue was purified by vacuum distillation

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2.36 g of ethyl N-(2,4-dichloro-1,3,5-triazin-6-yl)glycinate [obtained as described in Preparation 4(A)], 4.19 g of 2,2,6,6-tetramethyl-4-(butylamino)piperidine [obtained as described in Preparation i(A)] and 2.77 g of sodium bicarbonate were heated under reflux in 20 ml of xylene for 29 hours. At the end of this time, the xylene was removed by distillation under reduced pressure, and a mixture of methylene chloride and water was added to the resulting residue, after which the mixture was shaken. The methylene chloride layer was separated, dried and concentrated by evaporation under reduced pressure, and the resulting residue was purified by silica gel column chromatography (using a 20:10:1:1 by volume mixture of hexane, diethyl ether, ethanol and triethylamine as eluent), to yield 5.46 g of the title compound melting at 40° C. At the end of this time, the xylene was removed by distillation under reduced pressure a mixture of methylene chloride and water was added to the resulting residue The methylene chloride layer was separated dried concentrated by evaporation under reduced pressure the resulting residue was purified by silica gel column chromatography ( by volume mixture of hexane, diethyl ether, ethanol and triethylamine as eluent),

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2.36 g of ethyl N-(2,4-dichloro-1,3,5-triazin-6-yl)glycinate [obtained as described in Preparation 4(A)], 4.19 g of 2,2,6,6-tetramethyl-4-(butylamino)piperidine [obtained as described in Preparation i(A)] and 2.77 g of sodium bicarbonate were heated under reflux in 20 ml of xylene for 29 hours. At the end of this time, the xylene was removed by distillation under reduced pressure, and a mixture of methylene chloride and water was added to the resulting residue, after which the mixture was shaken. The methylene chloride layer was separated, dried and concentrated by evaporation under reduced pressure, and the resulting residue was purified by silica gel column chromatography (using a 20:10:1:1 by volume mixture of hexane, diethyl ether, ethanol and triethylamine as eluent), to yield 5.46 g of the title compound melting at 40° C. At the end of this time, the xylene was removed by distillation under reduced pressure a mixture of methylene chloride and water was added to the resulting residue The methylene chloride layer was separated dried concentrated by evaporation under reduced pressure the resulting residue was purified by silica gel column chromatography ( by volume mixture of hexane, diethyl ether, ethanol and triethylamine as eluent),