Morpholine → 3-morpholin-4-ylcyclohex-2-en-1-one

HRID 1657090Notes

Reaction equation

HRID 1657090 reaction equation
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][C:3](=[O:7])[CH2:2]1.[NH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1>C1C=CC=CC=1>[O:12]1[CH2:13][CH2:14][N:9]([C:1]2[CH2:6][CH2:5][CH2:4][C:3](=[O:7])[CH:2]=2)[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 104341,3-Cyclohexanedione

Product 1

HCID 43733443-morpholin-4-ylcyclohex-2-en-1-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In 700 ml benzene was dissolved 40.0 g 1,3-cyclohexanedione and 62 ml morpholine. The resulting solution was heated at reflux under nitrogen atmosphere for 1.5 hours. The water present in the reaction mixture was collected using a Dean-Stark trap. Upon cooling to room temperature, the reaction mixture was filtered through alumina and the filtrate concentrated in vacuo. Trituration of the resulting oil with ether solidified 62.4 g of 3-morpholino-2-cyclohexen-1-one crystals.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux under nitrogen atmosphere for 1.5 hours
  3. customThe water present in the reaction mixture was collected
  4. filtrationthe reaction mixture was filtered through alumina
  5. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-136fb703968e4e2c9b541b632f1c4860
Source dataset
uspto-grants-1993_10
Patent number
US05256672

Reaction notes

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