Water → 1-Cyclohexyloxy-2,2,6,6-tetramethyl-4-acetoxypiperidine

HRID 52388

Reaction equation

HRID 52388 reaction equation
[C:1]([O:4][CH:5]1[CH2:10][C:9]([CH3:12])([CH3:11])[NH:8][C:7]([CH3:14])([CH3:13])[CH2:6]1)(=[O:3])[CH3:2].[OH2:15].[CH2:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>[Mo]=O>[CH:16]1([O:15][N:8]2[C:7]([CH3:14])([CH3:13])[CH2:6][CH:5]([O:4][C:1](=[O:3])[CH3:2])[CH2:10][C:9]2([CH3:12])[CH3:11])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 962WaterHCID 8078CyclohexaneHCID 141497154-Acetoxy-2,2,6,6-tetramethylpiperidine

Product 1

HCID 196988861-Cyclohexyloxy-2,2,6,6-tetramethyl-4-acetoxypiperidine

Reagents, catalysts & solvents 1

HCID 139765Molybdenum oxideCatalyst

Conditions

Temperature
25 °C

Procedure

60 g (301 mmol) of 4-acetoxy-2,2,6,6-tetramethylpiperidine are dissolved in 300 ml of cyclohexane under nitrogen in a 1.5 l sulfonation flask fitted with magnetic stirrer, water separator, thermometer and dropping funnel. 4.3 g (30 mmol) of molybdenum oxide are added. 154 g (1.2 mol) of an aqueous 70% solution of t-butyl hydroperoxide are extracted three times with 35 ml of cyclohexane in each case, and the organic phase is dried over sodium sulfate and transferred into the dropping funnel. The reaction mixture is warmed to reflux, and the t-butyl hydroperoxide solution is added dropwise over the course of 2 hours. After a further 2 hours, the elimination of water is complete. The mixture is held at the reflux temperature overnight and is then cooled to 25° C., and the catalyst is filtered off. Ice is added, a little sodium sulfite is added in order to destroy the excess hydroperoxide, and the organic phase is then separated off, washed with water and dried over sodium sulfate, and the solvent is removed on a Rotavap.

Workup

  1. customfitted with magnetic stirrer
  2. extraction154 g (1.2 mol) of an aqueous 70% solution of t-butyl hydroperoxide are extracted three times with 35 ml of cyclohexane in each case
  3. dry with materialthe organic phase is dried over sodium sulfate
  4. temperatureThe reaction mixture is warmed
  5. temperatureto reflux
  6. additionthe t-butyl hydroperoxide solution is added dropwise over the course of 2 hours
  7. customis held at the reflux temperature overnight
  8. filtrationthe catalyst is filtered off
  9. additionIce is added
  10. additiona little sodium sulfite is added in order
  11. customto destroy the excess hydroperoxide
  12. customthe organic phase is then separated off
  13. washwashed with water
  14. dry with materialdried over sodium sulfate
  15. customthe solvent is removed on a Rotavap

Sources & evidence

ORD record
ord-794b65abecf44a6db554c7d58fadf8bc
Source dataset
uspto-grants-1997_04
Patent number
US05616637

Linked notes

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