Benzyl Bromide → HCID 20393556, compound

HRID 1862927Notes

Reaction equation

HRID 1862927 reaction equation
[OH:1][CH:2]([CH2:39][N:40]([CH2:51][CH2:52][OH:53])[CH:41]1[CH2:46][C:45]([CH3:48])([CH3:47])[NH:44][C:43]([CH3:50])([CH3:49])[CH2:42]1)[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH:22]([OH:38])[CH2:23][N:24]([CH:28]3[CH2:33][C:32]([CH3:35])([CH3:34])[NH:31][C:30]([CH3:37])([CH3:36])[CH2:29]3)[CH2:25][CH2:26][OH:27])=[CH:16][CH:15]=2)([CH3:13])[CH3:12])=[CH:7][CH:6]=1.[H-].[Na+].[CH2:56](Br)[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1>CN(C)C=O>[CH2:56]([O:38][CH:22]([CH2:23][N:24]([CH2:25][CH2:26][O:27][CH2:11][C:8]1[CH:9]=[CH:10][CH:5]=[CH:6][CH:7]=1)[CH:28]1[CH2:33][C:32]([CH3:35])([CH3:34])[NH:31][C:30]([CH3:37])([CH3:36])[CH2:29]1)[CH2:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C:11]([C:8]2[CH:7]=[CH:6][C:5]([O:4][CH2:3][CH:2]([O:1][CH2:56][C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)[CH2:39][N:40]([CH:41]3[CH2:42][C:43]([CH3:50])([CH3:49])[NH:44][C:45]([CH3:48])([CH3:47])[CH2:46]3)[CH2:51][CH2:52][O:53][CH2:56][C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)=[CH:10][CH:9]=2)([CH3:13])[CH3:12])=[CH:15][CH:16]=1)[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 20393551HCID 20393551, compound

Product 1

HCID 20393556HCID 20393556, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 7.4 g of 2,2-bis[4-{2-hydroxy-3-[N-(2-hydroxyethyl)-N-(2,2,6,6-tetramethyl-4-piperidyl)amino]propoxy}phenyl]propane, obtained as described in Example 17, and 1.44 g of sodium hydride in 150 ml of N,N-dimethylformamide was heated, with stirring, at 70°-80° C. for 2 hours. The reaction mixture was then cooled to ambient temperature and 10.3 g of benzyl bromide were added. The mixture was then heated, with stirring, at 100°-110° C. for 4 hours. At the end of this time, the solvent was removed from the reaction mixture by evaporation in vacuo, and the residue was dissolved in benzene and the benzene solution was washed, in turn, with a 5% w/w aqueous solution of sodium carbonate and with water. The washed solution was then dried over anhydrous potassium carbonate. The solvent was removed from the benzene solution by evaporation under reduced pressure and the residue thus obtained was purified by column chromatography through silica gel eluted with a 20:4:2:1 by volume mixture of ethyl acetate, benzene, ethanol and triethylamine. The desired compound was obtained in the form of an pale yellow, very viscous product having an Rf value of 0.32 on thin layer chromatography on silica gel developed with a 20:4:2:1 by volume mixture of ethyl acetate, benzene, ethanol and triethylamine.

Workup

  1. customobtained
  2. temperaturewas heated
  3. temperatureThe mixture was then heated
  4. stirringwith stirring, at 100°-110° C. for 4 hours
  5. customAt the end of this time, the solvent was removed from the reaction mixture by evaporation in vacuo
  6. dissolutionthe residue was dissolved in benzene
  7. washthe benzene solution was washed, in turn, with a 5% w/w aqueous solution of sodium carbonate and with water
  8. dry with materialThe washed solution was then dried over anhydrous potassium carbonate
  9. customThe solvent was removed from the benzene solution by evaporation under reduced pressure
  10. customthe residue thus obtained
  11. customwas purified by column chromatography through silica gel
  12. washeluted with a 20:4:2:1 by volume mixture of ethyl acetate, benzene, ethanol and triethylamine

Sources & evidence

ORD record
ord-ee604b32fc94419381088403e68808a9
Source dataset
uspto-grants-1979_09
Patent number
US04166813

Reaction notes

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