Cyclohexene oxide → (1R,2R)-2-(Cyclopropylamino)cyclohexan-1-ol

HRID 1856751Notes

Reaction equation

HRID 1856751 reaction equation
[CH:1]12[O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6]2.[CH:8]1([NH2:11])[CH2:10][CH2:9]1>CO>[OH:7][C@@H:1]1[CH2:6][CH2:5][CH2:4][CH2:3][C@H:2]1[NH:11][CH:8]1[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 9246Cyclohexene oxideHCID 69828Cyclopropylamine

Product 1

HCID 15479724(1R,2R)-2-(Cyclopropylamino)cyclohexan-1-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Cyclohexene oxide (143 ml) and cyclopropylamine (82 g) are dissolved in methanol (1 liter), and the mixture is refluxed for 5 hours. The mixture is concentrated under reduced pressure to remove the solvent, and the resulting residue is distilled under reduced pressure to give trans-N-(2-hydroxycyclohexyl)-N-cyclopropylamine (126 g) as a colorless oil.

Workup

  1. temperaturethe mixture is refluxed for 5 hours
  2. concentrationThe mixture is concentrated under reduced pressure
  3. customto remove the solvent
  4. distillationthe resulting residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-6cccfe0ff9764b06abfd900d269d4b11
Source dataset
uspto-grants-2000_11
Patent number
US06143763

Reaction notes

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