Benzene → 4-Methylcarbamoyloxy-1,2,2,6,6-pentamethylpiperidine

HRID 2397246Notes

Reaction equation

HRID 2397246 reaction equation
[CH3:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH:5]([OH:10])[CH2:4][C:3]1([CH3:12])[CH3:11].[CH3:13][N:14]=[C:15]=[O:16].N12CCN(CC1)CC2.C1C=CC=CC=1>O>[CH3:13][NH:14][C:15]([O:10][CH:5]1[CH2:6][C:7]([CH3:8])([CH3:9])[N:2]([CH3:1])[C:3]([CH3:12])([CH3:11])[CH2:4]1)=[O:16]

Participants

6

Reactant 4

HCID 241BenzeneHCID 9237DabcoHCID 12228Methyl IsocyanateHCID 754724-Piperidinol, 1,2,2,6,6-pentamethyl-

Product 1

HCID 204924944-Methylcarbamoyloxy-1,2,2,6,6-pentamethylpiperidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 16.4 parts of 1,2,2,6,6-pentamethylpiperidin-4-ol, 6.27 parts of methyl isocyanate and 0.5 parts of 1,4-diazabicyclo[2,2,2]octane was refluxed in 150 parts of dry benzene for 24 hours. Removal of the benzene solvent by distillation under reduced pressure yielded an oily solid which was poured on to 200 parts of water and allowed to stand for 24 hours. The solid formed was collected by filtration, dried and crystallised from n-hexane to give 14.2 parts of 4-methylcarbamoyloxy-1,2,2,6,6-pentamethylpiperidine having a melting point of 96°-7° C. and the following elemental analysis by weight:

Workup

  1. customRemoval of the benzene solvent
  2. distillationby distillation under reduced pressure
  3. customyielded an oily solid which
  4. customThe solid formed
  5. filtrationwas collected by filtration
  6. customdried
  7. customcrystallised from n-hexane

Sources & evidence

ORD record
ord-65b5d11af4834d57bd1162d8d74123ab
Source dataset
uspto-grants-1977_05
Patent number
US04021432

Reaction notes

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