Ethanol → HCID 86734587, compound

HRID 597551Notes

Reaction equation

HRID 597551 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.Br[CH2:13][C:14](OCC)=[O:15].[CH2:19]([OH:21])[CH3:20]>>[CH2:19]([O:21][N:3]1[C:4]([CH3:10])([CH3:9])[CH2:5][CH:6]([OH:8])[CH:7]([CH:13]=[C:14]=[O:15])[C:2]1([CH3:11])[CH3:1])[CH3:20]

Participants

4

Reactant 3

HCID 702EthanolHCID 7748Ethyl bromoacetateHCID 754714-Hydroxy-2,2,6,6-tetramethylpiperidine

Product 1

HCID 86734587HCID 86734587, compound

Procedure

A mixture of 15.7 parts of 2,2,6,6-tetramethylpiperidin-4-ol and 8.3 parts of ethyl bromoacetate in 50 parts of ethyl alcohol was heated at reflux for 48 hours. The cooled reaction mixture was filtered to remove 2,2,6,6-tetramethylpiperidin-4-ol hydrobromide and the solvent removed by distillation in vacuo. The residue was triturated with 40°-60°C petroleum ether to remove the unreacted 2,2,6,6-tetramethylpiperidin-4-ol. The filtrate was then distilled under reduced pressure to yield pure 1-ethoxy-carbonylmethyl-2,2,6,6-tetramethylpiperidin-4-ol as a colourless liquid (of boiling point 116°C at 0.2 mm) which slowly solidified on standing (melting point 42°-42.5°C). This material gave the following elemental analysis by weight:

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 48 hours
  3. customThe cooled reaction mixture
  4. filtrationwas filtered
  5. customto remove 2,2,6,6-tetramethylpiperidin-4-ol hydrobromide
  6. customthe solvent removed by distillation in vacuo
  7. customThe residue was triturated with 40°-60°C petroleum ether
  8. customto remove the unreacted 2,2,6,6-tetramethylpiperidin-4-ol
  9. distillationThe filtrate was then distilled under reduced pressure

Sources & evidence

ORD record
ord-4649275a84894c0f8ace921b2342e252
Source dataset
uspto-grants-1977_03
Patent number
US04014887

Reaction notes

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