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

HRID 862872Notes

Reaction equation

HRID 862872 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 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 warmed to 50°-55° C., and 90.7 g (980 mmol) of epichlorohydrin are added dropwise over the course of 45 minutes, during which the mixture is stirred vigorously. The mixture is stirred at 55° C. for a further 3 hours and then poured into 1 litre of ice water, and the organic phase is separated off and washed once with water. The organic phase is dried over sodium sulfate, decoloured using activated charcoal, filtered and evaporated. The residue is distilled over a Vigreux column: boiling point 116°-117° C./0.06 mmHg.

Workup

  1. customfitted with stirrer
  2. additionare added
  3. temperatureThe mixture is warmed to 50°-55° C.
  4. stirringThe 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-bab0485e487243bcb63e86125f134d90
Source dataset
uspto-grants-1998_02
Patent number
US05719257

Reaction notes

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