Water → Morpholine, 4-(1-cyclohexen-1-yl)-

HRID 262541Notes

Reaction equation

HRID 262541 reaction equation
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.C1(C)C(S(O)(=O)=O)=CC=CC=1.O>C1C=CC=CC=1>[O:11]1[CH2:12][CH2:13][N:8]([C:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=2)[CH2:9][CH2:10]1

Participants

6

Reactant 4

HCID 962WaterHCID 69252-Methylbenzenesulfonic acidHCID 7967CyclohexanoneHCID 8083Morpholine

Product 1

HCID 69589Morpholine, 4-(1-cyclohexen-1-yl)-

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

295g of cyclohexanone and 261 g of morpholine are dissolved in 800ml of benzene. After the whole has been dissolved, 1.5g of p. toluene sulphonic acid are added and the mixture is heated under reflux. The water formed is extracted continuously by azeotropic distillation. After 20 hours reflux, the remaining solvent is distilled off and the oily residue is recovered. 379 g of the enamine are so obtained, boiling under 2mm at 115° to 117°. The yield amounts to 76%.

Workup

  1. dissolutionAfter the whole has been dissolved
  2. temperaturethe mixture is heated
  3. temperatureunder reflux
  4. extractionis extracted continuously by azeotropic distillation
  5. temperatureAfter 20 hours reflux
  6. distillationthe remaining solvent is distilled off
  7. customthe oily residue is recovered

Sources & evidence

ORD record
ord-66d5b427a6b642e1927c729c78c4d2f6
Source dataset
uspto-grants-1979_05
Patent number
US04154851

Reaction notes

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