Morpholine → 4-Isopropenyl-1-methyl-2-morpholin-4-yl-cyclohexanol

HRID 1966011Notes

Reaction equation

HRID 1966011 reaction equation
[CH3:1][C:2]([CH:4]1[CH2:9][CH:8]2[O:10][C:7]2([CH3:11])[CH2:6][CH2:5]1)=[CH2:3].[Cl-].[Li+].[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1>C(O)C>[C:2]([CH:4]1[CH2:5][CH2:6][C:7]([CH3:11])([OH:10])[CH:8]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH2:9]1)([CH3:1])=[CH2:3]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 91496Limonene oxideHCID 433294Lithium Chloride

Product 1

HCID 226252054-Isopropenyl-1-methyl-2-morpholin-4-yl-cyclohexanolYield 49.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(+)-Limonene oxide (13.2 g, 0.087 moles) was dissolved in ethanol (40 ml) and lithium chloride (5.9 g, 0.14 moles) was added with stirring. Morpholine (11.4 g, 0.13 moles) was added and the reaction mixture was heated at 60° for 48 hours. The solvent was evaporated under reduced pressure and the residue taken up in dichloromethane. Washed with water. Extracted into 2M hydrochloric acid and washed with dichloromethane. Basified to pH 10 by addition of 2M sodium hydroxide. Extracted with diethyl ether and washed with water. Dried over anhydrous magnesium sulphate and evaporated the solvent under reduced pressure to give the product as a yellow oil (10.3 g)

Workup

  1. temperaturethe reaction mixture was heated at 60° for 48 hours
  2. customThe solvent was evaporated under reduced pressure
  3. washWashed with water
  4. extractionExtracted into 2M hydrochloric acid
  5. washwashed with dichloromethane
  6. additionBasified to pH 10 by addition of 2M sodium hydroxide
  7. extractionExtracted with diethyl ether
  8. washwashed with water
  9. dry with materialDried over anhydrous magnesium sulphate
  10. customevaporated the solvent under reduced pressure

Sources & evidence

ORD record
ord-e86722f2cae44041a411c5da6e5745ef
Source dataset
uspto-grants-2013_04
Patent number
US08420637B2

Reaction notes

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