Phenyl isocyanate → Bis{3-[N-butyl-N-(2,2,6,6-tetramethyl-4-piperidyl)amino]-2-phenylcarbamoyloxypropyl}1,2-cyclohexanedicarboxylate

HRID 1862926Notes

Reaction equation

HRID 1862926 reaction equation
[CH2:1]([N:5]([CH2:16][CH:17]([OH:50])[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]([OH:49])[CH2:33][N:34]([CH2:45][CH2:46][CH2:47][CH3:48])[CH:35]1[CH2:40][C:39]([CH3:42])([CH3:41])[NH:38][C:37]([CH3:44])([CH3:43])[CH2:36]1)=[O:29])=[O:21])[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].[C:51]1([N:57]=[C:58]=[O:59])[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1>C1C=CC=CC=1>[CH2:1]([N:5]([CH2:16][CH:17]([O:50][C:58](=[O:59])[NH:57][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=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]([O:49][C:58](=[O:59])[NH:57][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[CH2:33][N:34]([CH2:45][CH2:46][CH2:47][CH3:48])[CH:35]1[CH2:40][C:39]([CH3:42])([CH3:41])[NH:38][C:37]([CH3:44])([CH3:43])[CH2:36]1)=[O:29])=[O:21])[CH:6]1[CH2:11][C:10]([CH3:13])([CH3:12])[NH:9][C:8]([CH3:14])([CH3:15])[CH2:7]1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 86736634Bis{3-[N-butyl-N-(2,2,6,6-tetramethyl-4-piperidyl)amino]-2-hydroxypropyl}1,2-cyclohexanedicarboxylate

Product 1

HCID 86736635Bis{3-[N-butyl-N-(2,2,6,6-tetramethyl-4-piperidyl)amino]-2-phenylcarbamoyloxypropyl}1,2-cyclohexanedicarboxylate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2.4 g of bis{3-[N-butyl-N-(2,2,6,6-tetramethyl-4-piperidyl)amino]-2-hydroxypropyl}1,2-cyclohexanedicarboxylate, obtained as described in Example 18, and 2.4 g of phenylisocyanate in 30 ml of benzene was refluxed, with stirring, for 3 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 vitreous mass having an Rf value of 0.58 on thin layer chromatography on silica gel developed with a 5:1 by volume mixture of ethyl acetate and triethylamine.

Workup

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

Sources & evidence

ORD record
ord-a7f8f168974f43b487ec7b1539632e9d
Source dataset
uspto-grants-1979_09
Patent number
US04166813

Reaction notes

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