1-Bromododecane → 2,2-Bis{4-[2-dodecyloxy-3-(7,7,8,9,9-pentamethyl-2,4-dioxo-1,3,8-triazaspiro[4.5]dec-3-yl)propoxy]phenyl}propane

HRID 972023Notes

Reaction equation

HRID 972023 reaction equation
[H-].[Na+].[OH:3][CH:4]([CH2:44][N:45]1[C:49](=[O:50])[C:48]2([CH2:55][C:54]([CH3:57])([CH3:56])[N:53]([CH3:58])[C:52]([CH3:60])([CH3:59])[CH2:51]2)[NH:47][C:46]1=[O:61])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH:24]([OH:43])[CH2:25][N:26]3[C:30](=[O:31])[C:29]4([CH2:36][C:35]([CH3:38])([CH3:37])[N:34]([CH3:39])[C:33]([CH3:41])([CH3:40])[CH2:32]4)[NH:28][C:27]3=[O:42])=[CH:18][CH:17]=2)([CH3:15])[CH3:14])=[CH:9][CH:8]=1.[CH2:62](Br)[CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH3:73]>CN(C)C=O>[CH2:62]([O:43][CH:24]([CH2:25][N:26]1[C:30](=[O:31])[C:29]2([CH2:36][C:35]([CH3:37])([CH3:38])[N:34]([CH3:39])[C:33]([CH3:40])([CH3:41])[CH2:32]2)[NH:28][C:27]1=[O:42])[CH2:23][O:22][C:19]1[CH:20]=[CH:21][C:16]([C:13]([C:10]2[CH:9]=[CH:8][C:7]([O:6][CH2:5][CH:4]([O:3][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:13][CH2:10][CH2:9][CH2:8][CH2:7][CH2:12][CH3:11])[CH2:44][N:45]3[C:49](=[O:50])[C:48]4([CH2:55][C:54]([CH3:57])([CH3:56])[N:53]([CH3:58])[C:52]([CH3:60])([CH3:59])[CH2:51]4)[NH:47][C:46]3=[O:61])=[CH:12][CH:11]=2)([CH3:15])[CH3:14])=[CH:17][CH:18]=1)[CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH3:73]

Participants

5

Reactant 3

HCID 89191-BromododecaneHCID 24758Sodium hydrideHCID 203967802,2-Bis{4-[2-hydroxy-3-(7,7,8,9,9-pentamethyl-2,4-dioxo-1,3,8-triazaspiro[4.5]dec-3-yl)propoxy]phenyl}propane

Product 1

HCID 203967962,2-Bis{4-[2-dodecyloxy-3-(7,7,8,9,9-pentamethyl-2,4-dioxo-1,3,8-triazaspiro[4.5]dec-3-yl)propoxy]phenyl}propane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.5 g of sodium hydride was added, with stirring, to a solution of 8.2 g of 2,2-bis{4-[2-hydroxy-3-(7,7,8,9,9-pentamethyl-2,4-dioxo-1,3,8-triazaspiro[4.5]dec-3-yl)propoxy]phenyl}propane, prepared as described in Example 1, in 150 ml of N,N-dimethylformamide, and the mixture was stirred at 50°-60° C. for 2 hours. 10.0 g of n-dodecyl bromide were then added dropwise to the mixture and the whole mixture was heated at 50°-60° C. for two hours and then at 70°-80° C. for a further 4 hours, stirring all the time. After completion of the reaction, the reaction mixture was condensed by evaporation under reduced pressure and then 200 ml of benzene were added to the resulting residue. This solution was then washed with, in turn, a 2% w/w aqueous solution of sodium carbonate and water. The washed solution was dried over anhydrous potassium carbonate and then the solvent was removed by evaporation under reduced pressure. The residue was purified by column chromatography through silica gel eluted with a 32:4:5:1 by volume mixture of ethyl acetate, benzene, ethanol and triethylamine, giving the desired Compound No. 34 as a colourless, viscous liquid, having an Rf value of 0.53 on thin-layer chromatography on silica gel using a 20:2:2:1 by volume mixture of ethyl acetate, benzene, ethanol and triethylamine as developing solvent.

Workup

  1. customprepared
  2. temperaturethe whole mixture was heated at 50°-60° C. for two hours
  3. waitat 70°-80° C. for a further 4 hours
  4. stirringstirring all the time
  5. customAfter completion of the reaction
  6. customcondensed
  7. customby evaporation under reduced pressure
  8. addition200 ml of benzene were added to the resulting residue
  9. washThis solution was then washed with, in turn
  10. dry with materialThe washed solution was dried over anhydrous potassium carbonate
  11. customthe solvent was removed by evaporation under reduced pressure
  12. customThe residue was purified by column chromatography through silica gel
  13. washeluted with a 32:4:5:1 by volume mixture of ethyl acetate, benzene, ethanol and triethylamine

Sources & evidence

ORD record
ord-8cbf8b52df814bd7b04ccf59f213607f
Source dataset
uspto-grants-1979_07
Patent number
US04162246

Reaction notes

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