Epichlorohydrin → 1-(Cyclohexyloxy)-2,2,6,6-tetramethyl-4-[(oxiran-2-yl)methoxy]piperidine

HRID 2210258Notes

Reaction equation

HRID 2210258 reaction equation
[OH-].[Na+].[CH:3]1([O:9][N:10]2[C:15]([CH3:17])([CH3:16])[CH2:14][CH:13]([OH:18])[CH2:12][C:11]2([CH3:20])[CH3:19])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[CH2:21]([CH:23]1[O:25][CH2:24]1)Cl>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH:3]1([O:9][N:10]2[C:11]([CH3:20])([CH3:19])[CH2:12][CH:13]([O:18][CH2:21][CH:23]3[O:25][CH2:24]3)[CH2:14][C:15]2([CH3:16])[CH3:17])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

7

Reactant 3

HCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 113228111-Cyclohexyloxy-2,2,6,6-tetramethyl-piperidin-4-ol

Product 1

HCID 544150951-(Cyclohexyloxy)-2,2,6,6-tetramethyl-4-[(oxiran-2-yl)methoxy]piperidine

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

78.4 g (1.96 mol) of sodium hydroxide are dissolved in 80 ml of water under argon in a 750 ml sulfonation flask fitted with a stirrer, thermometer and dropping funnel. 100 g (392 mmol) of 1-cyclohexyloxy-2,2,6,6-tetramethyl-4-hydroxypiperidine and 12.6 g (39.2 mmol) of tetrabutylammonium bromide, dissolved in 250 ml of toluene, are added. The mixture is heated to 50°-55° C., and 90.7 g (980 mmol) of epichlorohydrin are added dropwise in the course of 45 minutes. During this operation, the mixture is stirred vigorously. The reaction mixture is stirred at 55° C. for a further 3 hours. It is then poured onto 1 liter of ice-water and the organic phase is separated off and washed once with water. The organic phase is dried over sodium sulfate, decolorized with active charcoal, filtered and evaporated. The residue is distilled over a Vigreux column: boiling point 116°-117° C./0.06 mmHg.

Workup

  1. customfitted with a stirrer
  2. additionare added
  3. temperatureThe mixture is heated to 50°-55° C.
  4. stirringThe reaction mixture is stirred at 55° C. for a further 3 hours
  5. customthe organic phase is separated off
  6. washwashed once with water
  7. dry with materialThe organic phase is dried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. distillationThe residue is distilled over a Vigreux column

Sources & evidence

ORD record
ord-9d9c9a68a6c2494093458e72e920744f
Source dataset
uspto-grants-1995_10
Patent number
US05457204

Reaction notes

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