Triethylene Glycol → 4-(4-Ethylphenoxy)piperidine

HRID 463325Notes

Reaction equation

HRID 463325 reaction equation
[C:1]([C:4]1[CH:16]=[CH:15][C:7]([O:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:6][CH:5]=1)(=O)[CH3:2].C([O-])(=O)C([O-])=O.[OH-].[K+].O.NN.C(O)COCCOCCO>>[CH2:1]([C:4]1[CH:16]=[CH:15][C:7]([O:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:6][CH:5]=1)[CH3:2]

Participants

6

Reactant 5

HCID 8172Triethylene GlycolHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 71081OxalateHCID 134574271-{4-[(Piperidin-4-yl)oxy]phenyl}ethan-1-one

Product 1

HCID 134574294-(4-Ethylphenoxy)piperidineYield 38.6%

Procedure

A solution of 4-(4-acetylphenoxy)piperidine (liberated from 15.0 g, 48.5 mmol, of the oxalate), 7.45 g of potassium hydroxide, 5.39 ml of 85% hydrazine hydrate and 54 ml of triethyleneglycol was stirred at reflux for 1 hour. The mixture was then cooled to room temperature and the flask fitted with a distillation apparatus. The temperature was then raised to 190°-195° and water removed by distillation. The mixture was stirred at 190°-195° for 3 hours and the mixture allowed to cool to room temperature. The mixture was diluted with water, extracted twice with ether and with 1N HCl, made basic with saturated sodium carbonate, extracted with ether and dried over potassium carbonate. Filtration followed by evaporation of the solvent provided an oil. Kugelrohr distillation at 114°-116°/1 mm provided 3.84 g (18.7 mmol, 38.6%) of 4-(4-ethylphenoxy)piperidine, m.p. 37-41.

Workup

  1. temperatureat reflux for 1 hour
  2. customthe flask fitted with a distillation apparatus
  3. temperatureThe temperature was then raised to 190°-195°
  4. customwater removed by distillation
  5. stirringThe mixture was stirred at 190°-195° for 3 hours
  6. temperatureto cool to room temperature
  7. additionThe mixture was diluted with water
  8. extractionextracted twice with ether and with 1N HCl
  9. extractionextracted with ether
  10. dry with materialdried over potassium carbonate
  11. filtrationFiltration
  12. customfollowed by evaporation of the solvent
  13. customprovided an oil
  14. distillationKugelrohr distillation at 114°-116°/1 mm

Sources & evidence

ORD record
ord-252253e7c675432f96f0686e96717777
Source dataset
uspto-grants-1985_05
Patent number
US04518713

Reaction notes

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