Phenyl isocyanate → HCID 20492382, compound

HRID 2397249Notes

Reaction equation

HRID 2397249 reaction equation
[C:1]1([NH:7][C:8]([O:10][CH:11]2[CH2:16][C:15]([CH3:18])([CH3:17])[N:14]([CH2:19][CH:20]([OH:27])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:13]([CH3:29])([CH3:28])[CH2:12]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:30]1([N:36]=[C:37]=[O:38])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.N12CCN(CC1)CC2>C1C=CC=CC=1>[C:1]1([NH:7][C:8]([O:10][CH:11]2[CH2:16][C:15]([CH3:18])([CH3:17])[N:14]([CH2:19][CH:20]([O:27][C:37](=[O:38])[NH:36][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:13]([CH3:29])([CH3:28])[CH2:12]2)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 9237DabcoHCID 20492274HCID 20492274, compound

Product 1

HCID 20492382HCID 20492382, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 3.0 parts of the product from Example 81, 0.90 parts of phenyl isocyanate and 0.1 parts of 1,4-diazabicyclo[2,2,2]octane in 25 parts of dry benzene was heated under reflux conditions for 24 hours. The benzene solvent was removed by distillation under reduced pressure and the residue crystallised from petroleum ether (b.p. 60°-80° C.) to give 4-phenylcarbamoyloxy-1-[2'-(phenylcarbamoyloxy)-2'-phenylethyl]-2,2,6,6-tetramethylpiperidine having a melting point of 173° C. and the following elemental analysis by weight:

Workup

  1. temperaturewas heated under reflux conditions for 24 hours
  2. customThe benzene solvent was removed by distillation under reduced pressure
  3. customthe residue crystallised from petroleum ether (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-b87c69396fcd415bad3c74c2c2970a88
Source dataset
uspto-grants-1977_05
Patent number
US04021432

Reaction notes

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