Cyclohexane-1,2-dicarboxylic acid bis(oxiranylmethyl) ester → Bis[2-hydroxy-3-(4-hydroxy-2,2,6,6-tetramethylpiperidino)propyl]1,2-cyclohexanedicarboxylate

HRID 1758188Notes

Reaction equation

HRID 1758188 reaction equation
[OH:1][CH:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[NH:5][C:4]([CH3:11])([CH3:10])[CH2:3]1.[O:12]1[CH2:31][CH:13]1[CH2:14][O:15][C:16]([CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1[C:24]([O:26][CH2:27][CH:28]1[O:30][CH2:29]1)=[O:25])=[O:17]>C1C=CC=CC=1>[OH:12][CH:13]([CH2:31][N:5]1[C:6]([CH3:8])([CH3:9])[CH2:7][CH:2]([OH:1])[CH2:3][C:4]1([CH3:11])[CH3:10])[CH2:14][O:15][C:16]([CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1[C:24]([O:26][CH2:27][CH:28]([OH:30])[CH2:29][N:5]1[C:4]([CH3:11])([CH3:10])[CH2:3][CH:2]([OH:1])[CH2:7][C:6]1([CH3:9])[CH3:8])=[O:25])=[O:17]

Participants

4

Reactant 2

HCID 21660Cyclohexane-1,2-dicarboxylic acid bis(oxiranylmethyl) esterHCID 754714-Hydroxy-2,2,6,6-tetramethylpiperidine

Product 1

HCID 86738787Bis[2-hydroxy-3-(4-hydroxy-2,2,6,6-tetramethylpiperidino)propyl]1,2-cyclohexanedicarboxylate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 11.0 g of 4-hydroxy-2,2,6,6-tetramethylpiperidine and 7.0 g of bis(2,3-epoxypropyl)1,2-cyclohexanedicarboxylate was heated, with stirring, at 170°-180° C. for 5 hours. After completion of the reaction, benzene was added to the reaction mixture and then the benzene solution was washed with water and dried over anhydrous potassium carbonate. The solvent was evaporated under reduced pressure from the benzene solution, leaving a residue, which was then purified by column chromatography through silica gel eluted with a 16:2:1:1 by volume mixture of ethyl acetate, benzene, ethanol and triethylamine, giving the desired Compound No. 90 as a vitreous solid. The Compound had an Rf value of 0.32 on thin-layer chromatography on silica gel developed with a 16:2:3:1 by volume mixture of ethyl acetate, benzene, ethanol and triethylamine.

Workup

  1. temperaturewas heated
  2. additionwas added to the reaction mixture
  3. washthe benzene solution was washed with water
  4. dry with materialdried over anhydrous potassium carbonate
  5. customThe solvent was evaporated under reduced pressure from the benzene solution
  6. customleaving a residue, which
  7. customwas then purified by column chromatography through silica gel
  8. washeluted with a 16:2:1:1 by volume mixture of ethyl acetate, benzene, ethanol and triethylamine

Sources & evidence

ORD record
ord-ee22b69748ff4768a121917b54e2e5a7
Source dataset
uspto-grants-1983_02
Patent number
US04371644

Reaction notes

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