49  US 6,872,832 B2  50  EXAMPLE 45  EXAMPLE  44  EXAMPLE 43  EXAMPLE 44C  EXAMPLE 42  EXAMPLE 41  EXAMPLE 40  EXAMPLE 44B  EXAMPLE 44A  EXAMPLE 39  EXAMPLE 38  EXAMPLE 37  A  mixture of  N,N’,N"  ,N"’-tetrakis{2,4-bis[N-(1-oxyl-2,2,  6,6-tetramethy lpiperidin-4-y  1 ]buty lamina ]-s-triazinyl }-3,3’- Reaction of  N,N’,N"  ,N"’-Tetrakis{2,4-bis[N-(1-oxyl- 2,2,6,6-tetramethylpiperidin-4-yl]butylamino ]-s› triazin-6-y 1  }-3,3 ’-ethy lenediiminodipropylamine  with Cyclohexanol  A  mixture of 12.11 g (49.4 mmol) of the compound  obtained in Example 16A, 12.11 g (44.8 mmol) of methyl  l-(2-Hydroxy-2-methylpropoxy)-4- hexadecanoyloxy-2,2,6,6-tetramethylpiperidine  Aqueous hydrogen peroxide is added to a mixture of  4-hydroxy-l-oxyl-2,2,6,6-tetramethylpiperidine and ferrous  chloride tetrahydrate in 2-ethyl-1-hexanol according to the  procedure of Example 25.  Reaction-of-4-Hydroxy-l-oxyl-2,2,6,6- tetramethylpiperidine with 2-Ethyl-1-hexanol  A mixture of 72.7 g (0.297 mol) of the compound  obtained in Example 16A, 51.9 g (0.242 mol) of methyl  dodecanoate (methyl laurate), 0.43 g of lithium amide, and  toluene is heated at reflux. Methanol is distilled from the  reaction mixture along with some of the toluene. The  reaction mixture is quenched with dilute acetic acid, and  washed successively with aqueous methanol, dilute aqueous  sodium bicarbonate solution, and saturated sodium chloride  solution. The toluene solution is dried over magnesium  sulfate, filtered, and concentrated to obtain a solid. Purifi› cation by flash chromatography on silica gel with hexane/  ethyl acetate affords 96.7 g of the title compound as a white  solid, mp 46-8.  1-(2-hydroxy-2-methylpropoxy )-4-dodecanoy loxy-2,  2,6,6-tetramethylpiperidine  Aqueous hydrogen peroxide is added to a mixture of  l-oxyl-2,2,6,6-tetramethylpiperidin-4-one and ferrous chlo› ride tetrahydrate in glycerol according to the procedure of  Example 25.  Reaction of l-Oxyl-2,2,6,6-tetramethylpiperidin-4- one with Glycerol  Aqueous hydrogen peroxide is added to a mixture of  4-hexyloxy-l-oxyl-2,2,6,6-tetramethylpiperidine and fer› rous chloride tetrahydrate in pinacol according to the pro› cedure of Example 25.  Reaction of 4-Hexyloxy-l-oxyl-2,2,6,6- tetramethylpiperidine with Pinacol  A mixture of 51.6 g (0.210 mol) of the compound  obtained in Example 16A, 30.6 g (0.193 mol) of methyl  2-ethylhexanoate, 1.26 g of lithium amide, and toluene is  heated at reflux. Methanol is distilled from the reaction  mixture along with some of the toluene. The reaction  mixture is quenched with dilute acetic acid, and washed  successively with aqueous methanol, dilute aqueous sodium  bicarbonate solution, and saturated sodium chloride solu› tion. The toluene solution is dried over magnesium sulfate,  filtered, and concentrated to obtain a yellow liquid. Purifi› cation by flash chromatography on silica gel with hexane/  ethyl acetate affords 51.0 g of the title compound as a pale  yellow oil.  1-(2-hydroxy-2-methy lpropoxy )-4-(2- ethy lhexanoyloxy )-2,2,6,6-tetramethylpiperidine  A mixture of 8.40 g (34.2 mmol) of the compound  obtained in Example 16A, 10.17 g (31.1 mmol) of methyl  eicosanoate, 0.35 g of lithium amide, and toluene is heated  at reflux. The reaction mixture is quenched with dilute acetic  acid, and washed successively with aqueous methanol,  dilute aqueous sodium bicarbonate solution, and saturated  sodium chloride solution. The toluene solution is dried over  magnesium sulfate, filtered, and concentrated to obtain a  solid which is purified by flash chromatography on silica gel  with hexane/ethyl acetate to afford 9.9 g of the title com› pound as a white solid, mp 69-73.  Aqueous hydrogen peroxide is added to a mixture of  4-benzoyloxy-l-oxyl-2,2,6,6-tetramethylpiperidine and fer› rous chloride tetrahydrate in 1,4-butanediol according to the  procedure of Example 25.  Reaction of 4-Benzoyloxy-l-oxyl-2,2,6,6- tetramethylpiperidine with 1,4-Butanediol  Aqueous hydrogen peroxide is added to a mixture of  bis(l-oxyl-2,2,6,6-tetramethylpiperidin-4-yl) sebacate and  ferrous chloride tetrahydrate in isopropanol according to the  procedure of Example 25.  Reaction of Bis(l-oxyl-2,2,6,6-tetramethylpiperidin- 4-yl) Sebacate with Isopropanol  1-(2-hydroxy-2-methylpropoxy )-4-eicosanoyloxy-2,  2,6,6-tetramethylpiperidine  hexadecanoate (methyl palmitate), 0.76 g of lithium amide,  and toluene is heated at reflux. Methanol is distilled from the  reaction mixture along with some of the toluene. The  reaction mixture is quenched with dilute acetic acid, and  washed successively with aqueous methanol, dilute aqueous  sodium bicarbonate solution, and saturated sodium chloride  solution. The toluene solution is dried over magnesium  sulfate, filtered, and concentrated to obtain a solid. Purifi› cation by flash chromatography on silica gel with hexane/  ethyl acetate affords 18 g of a solid. Recrystallization from  methanol yields 10.7 g of the title compound as a white  solid, mp 60---64.  Tributyltin hydride is added dropwise to a solution of  2-iodoethanol and excess bis(l-oxyl-_2,2,6,6- tetramethylpiperidin-4-yl) sebacate in chlorobenzene. The  crude reaction mixture is passed through silica gel with  heptane and then heptane/ethyl acetate to afford the title  compound.  Bis[ 1-(2-hydroxyethoxy )-2,2,6,6- tetramethy lpiperidin-4-y l] Sebacate  Aqueous hydrogen peroxide is added to a mixture of  4-benzoyloxy-l-oxyl-2,2,6,6-tetramethylpiperidine and fer› rous chloride tetrahydrate in trimethylene glycol according  to the procedure of Example 25.  Reaction of 4-Benzoyloxy-l-oxyl-2,2,6,6- tetramethylpiperidine with Trimethylene Glycol 