Cyclohexane-1,2-dicarboxylic acid bis(oxiranylmethyl) ester → Bis{3-[N-butyl-N-(2,2,6,6-tetramethyl-4-piperidyl)amino]-2-hydroxypropyl}1,2-cyclohexanedicarboxylate

HRID 1862925Notes

Reaction equation

HRID 1862925 reaction equation
[CH2:1]([NH:5][CH:6]1[CH2:11][C:10]([CH3:13])([CH3:12])[NH:9][C:8]([CH3:15])([CH3:14])[CH2:7]1)[CH2:2][CH2:3][CH3:4].[O:16]1[CH2:35][CH:17]1[CH2:18][O:19][C:20]([CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]1[C:28]([O:30][CH2:31][CH:32]1[O:34][CH2:33]1)=[O:29])=[O:21]>C(O)(C)(C)C>[CH2:1]([N:5]([CH2:33][CH:32]([OH:34])[CH2:31][O:30][C:28]([CH:23]1[CH2:24][CH2:25][CH2:26][CH2:27][CH:22]1[C:20]([O:19][CH2:18][CH:17]([OH:16])[CH2:35][N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH:6]1[CH2:7][C:8]([CH3:14])([CH3:15])[NH:9][C:10]([CH3:13])([CH3:12])[CH2:11]1)=[O:21])=[O:29])[CH:6]1[CH2:7][C:8]([CH3:14])([CH3:15])[NH:9][C:10]([CH3:13])([CH3:12])[CH2:11]1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 21660Cyclohexane-1,2-dicarboxylic acid bis(oxiranylmethyl) esterHCID 118285n-Butyl-2,2,6,6-tetramethyl-4-piperidinamine

Product 1

HCID 86736634Bis{3-[N-butyl-N-(2,2,6,6-tetramethyl-4-piperidyl)amino]-2-hydroxypropyl}1,2-cyclohexanedicarboxylate

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of 5 g of 4-butylamino-2,2,6,6-tetramethylpiperidine and 3 g of bis(2,3-epoxypropyl)1,2-cyclohexanedicarboxylate in 10 ml of t-butanol was refluxed, with stirring, for 8 hours. At the end of this time, the solvent was removed from the reaction mixture by evaporation under reduced pressure and the resulting residue was purified by column chromatography through silica gel eluted with a 20:1 by volume mixture of ethyl acetate and triethylamine. The desired compound was obtained in the form of a pale yellow, viscous oil having an Rf value of 0.53 on thin layer chromatography on silica gel developed with a 5:1 by volume mixture of ethyl acetate and triethylamine.

Workup

  1. temperaturewas refluxed
  2. customAt the end of this time, the solvent was removed from the reaction mixture by evaporation under reduced pressure
  3. customthe resulting residue was purified by column chromatography through silica gel
  4. washeluted with a 20:1 by volume mixture of ethyl acetate and triethylamine

Sources & evidence

ORD record
ord-658256e83c9c41a08163f1e0d61cb59b
Source dataset
uspto-grants-1979_09
Patent number
US04166813

Reaction notes

Loading…