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

HRID 2238623

Reaction equation

HRID 2238623 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-67676341ca7b4f958a62e34f71a09993
Source dataset
uspto-grants-2010_05
Patent number
US07718830B2

Linked notes

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