Allyl bromide → 2,2,6,6-Tetramethyl-1-(prop-2-en-1-yl)piperidin-4-ol

HRID 597549Notes

Reaction equation

HRID 597549 reaction equation
[CH3:1][C:2]1([CH3:11])[CH2:7][CH:6]([OH:8])[CH2:5][C:4]([CH3:10])([CH3:9])[NH:3]1.[CH2:12](Br)[CH:13]=[CH2:14]>C(O)C>[CH2:14]([N:3]1[C:4]([CH3:10])([CH3:9])[CH2:5][CH:6]([OH:8])[CH2:7][C:2]1([CH3:11])[CH3:1])[CH:13]=[CH2:12]

Participants

4

Reactant 2

HCID 7841Allyl bromideHCID 754714-Hydroxy-2,2,6,6-tetramethylpiperidine

Product 1

HCID 129919752,2,6,6-Tetramethyl-1-(prop-2-en-1-yl)piperidin-4-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 78.5 parts of 2,2,6,6-tetramethylpiperidine-4-ol and 30.25 parts of allyl bromide in 250 parts of ethyl alcohol was heated under reflux conditions for 48 hours. The cooled reaction mixture was filtered to remove 2,2,6,6-tetramethylpiperidin-4-ol hydrobromide formed during the reaction and the ethyl alcohol solvent was removed by distillation under reduced pressure. The residue was triturated with cold petroleum ether (b.p. 40°-60°C) to remove a small amount of unreacted 2,2,6,6-tetramethylpiperidin-4-ol. Crystallisation of the residue from 40°-60°C petroleum ether gave 1-allyl-2,2,6,6-tetramethylpiperidin-4-ol having a melting point of 84°-5°C and the following elemental analysis by weight.

Workup

  1. temperaturewas heated under reflux conditions for 48 hours
  2. customThe cooled reaction mixture
  3. filtrationwas filtered
  4. customto remove 2,2,6,6-tetramethylpiperidin-4-ol hydrobromide
  5. customformed during the reaction
  6. customthe ethyl alcohol solvent was removed by distillation under reduced pressure
  7. customThe residue was triturated with cold petroleum ether (b.p. 40°-60°C)
  8. customto remove a small amount of unreacted 2,2,6,6-tetramethylpiperidin-4-ol
  9. customCrystallisation of the residue from 40°-60°C petroleum ether

Sources & evidence

ORD record
ord-26a3b5cfd5764d27950ff404cb4b3fb9
Source dataset
uspto-grants-1977_03
Patent number
US04014887

Reaction notes

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