Potassium Hydroxide → 1-Cyclohexyloxy-2,2,6,6-tetramethyl-piperidin-4-ol

HRID 52389Notes

Reaction equation

HRID 52389 reaction equation
[OH-].[K+].[CH:3]1([O:9][N:10]2[C:15]([CH3:17])([CH3:16])[CH2:14][CH:13]([O:18]C(=O)C)[CH2:12][C:11]2([CH3:23])[CH3:22])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1>CO>[CH:3]1([O:9][N:10]2[C:11]([CH3:22])([CH3:23])[CH2:12][CH:13]([OH:18])[CH2:14][C:15]2([CH3:17])[CH3:16])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 196988861-Cyclohexyloxy-2,2,6,6-tetramethyl-4-acetoxypiperidine

Product 1

HCID 113228111-Cyclohexyloxy-2,2,6,6-tetramethyl-piperidin-4-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

24 g (428 mmol) of potassium hydroxide are dissolved in 600 ml of methanol in a conical flask. 85 g (286 mmol) of 1-cyclohexyloxy-2,2,6,6-tetramethyl-4-acetoxypiperidine are poured into the warm solution with stirring. The mixture is subsequently poured onto ice and extracted with diethyl ether. After the diethyl ether solution has been dried over sodium sulfate, the ether is evaporated and the viscous residue is dissolved in 300 ml of warm acetonitrile. The solution is filtered and allowed to crystallize; yield: 50 g (68%). The colourless substance has a melting point of 78.5° C.; purity according to GC analysis: 96%.

Workup

  1. additionThe mixture is subsequently poured onto ice
  2. extractionextracted with diethyl ether
  3. dry with materialAfter the diethyl ether solution has been dried over sodium sulfate
  4. customthe ether is evaporated
  5. dissolutionthe viscous residue is dissolved in 300 ml of warm acetonitrile
  6. filtrationThe solution is filtered
  7. customto crystallize

Sources & evidence

ORD record
ord-11a9fe98919548ab93c362e6c3d18f58
Source dataset
uspto-grants-1997_04
Patent number
US05616637

Reaction notes

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