Cyclohexene oxide → 2-Piperidin-1-yl-cyclohexanol

HRID 1107569Notes

Reaction equation

HRID 1107569 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].[CH:14]12[O:20][CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19]2>O>[OH:20][CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH:14]1[N:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 9246Cyclohexene oxideHCID 11430Potassium CarbonateHCID 2723721Piperidine, hydrochloride (1:1)

Product 1

HCID 131196932-Piperidin-1-yl-cyclohexanolYield 102.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Piperidine hydrochloride (3.648 g, 30 mmol) was stirred in a mixture of 4.0 mL of water and 4.146 g of ground potassium carbonate. This mixture was heated to 90° C. and cyclohexene oxide (1.01 mL, 10 mmol) was added. The resulting mixture was heated at 100° C. for 18 hours. The reaction was cooled then filtered to remove carbonate salts. The filter cake was washed with 25 mL of diethyl ether and 50 mL of ethyl acetate. The filtrate and washings were combined and washed with brine (2×20 mL), dried over magnesium sulfate, filtered, and evaporated to give 1.875 g (>100%) of the title compound which was used without further purification. 1H NMR consistent with desired product.

Workup

  1. temperatureThe resulting mixture was heated at 100° C. for 18 hours
  2. temperatureThe reaction was cooled
  3. filtrationthen filtered
  4. customto remove carbonate salts
  5. washThe filter cake was washed with 25 mL of diethyl ether and 50 mL of ethyl acetate
  6. washwashed with brine (2×20 mL)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-e8877022c7ce4e6aab6f92095555c6c9
Source dataset
uspto-grants-2000_05
Patent number
US06060488

Reaction notes

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