4-Piperidinol, 1,2,2,6,6-pentamethyl- → HCID 20492431, compound

HRID 2397254Notes

Reaction equation

HRID 2397254 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].S(O[CH2:24][CH2:25][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(C1C=CC(C)=CC=1)(=O)=O>C1C=CC=CC=1.[Na]>[O:26]([CH2:25][CH2:24][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)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 2

HCID 754724-Piperidinol, 1,2,2,6,6-pentamethyl-HCID 41734412-phenoxyethyl 4-methylbenzenesulfonate

Product 1

HCID 20492431HCID 20492431, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 5360545SodiumSolvent

Procedure

30 parts of 1,2,2,6,6,-pentamethylpiperidin-4-ol were dissolved in 250 parts of benzene and 4 parts of sodium added. The solution was heated overnight at reflux temperature and then cooled. 38 parts of 2-phenoxyethanol tosylate were added dropwise and the solution heated at reflux for 5 hours. On cooling the precipitate was filtered off and the filtrate evaporated in vacuo. Treatment of the residue with dilute hydrochloric acid and then basification with dilute sodium hydroxide to a pH 10 was followed by extraction with ether. Evaporation afforded a pale yellow oil which was chromatographed on alumina to give 4-(2'-phenoxyethoxy)-1,2,2,6,6-pentamethylpiperidine as a colourless oil which gave the following elemental analysis by weight:

Workup

  1. additionadded
  2. temperatureThe solution was heated overnight
  3. temperatureat reflux temperature
  4. temperaturecooled
  5. temperaturethe solution heated
  6. temperatureat reflux for 5 hours
  7. temperatureOn cooling the precipitate
  8. filtrationwas filtered off
  9. customthe filtrate evaporated in vacuo
  10. extractionTreatment of the residue with dilute hydrochloric acid and then basification with dilute sodium hydroxide to a pH 10 was followed by extraction with ether
  11. customEvaporation
  12. customafforded a pale yellow oil which
  13. customwas chromatographed on alumina

Sources & evidence

ORD record
ord-5331a34df39f4f328b6ef1fa53b35cdc
Source dataset
uspto-grants-1977_05
Patent number
US04021432

Reaction notes

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