p-Toluenesulfonic acid → 4-Cyclohexyl 1-morpholyl cyclohex-1 ene

HRID 1284010Notes

Reaction equation

HRID 1284010 reaction equation
[CH2:1]1[CH2:6][CH2:5][C:4](=O)[CH2:3][CH2:2]1.[NH:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.[C:14]1(C)[CH:19]=[CH:18][C:17](S(O)(=O)=O)=[CH:16][CH:15]=1>C1C=CC=CC=1>[CH:4]1([CH:18]2[CH2:17][CH2:16][C:15]([N:8]3[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)=[CH:14][CH2:19]2)[CH2:5][CH2:6][CH2:1][CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7967CyclohexanoneHCID 8083Morpholine

Product 1

HCID 215152864-Cyclohexyl 1-morpholyl cyclohex-1 ene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

54 g of 4-cyclohexanone are dissolved in 90 ml benzene and 39 ml morpholine are added to the fresh solution, then a few crystals of p-toluene sulphonic acid. The whole is heated under reflux for 3 days while distilling off the water-benzene mixture. The remaining benzenic solution is evaporated to dryness under reduced pressure. The dry residue weighs 76.8 g and the raw product shows a melting point of 88°- 90°. The raw enamine is ground, then dried in vacuo to constant weight. 74.3 g of 4-cyclohexyl-1-morpholyl-cyclohex-1-ene are recovered and used without further purification for the next step of the synthesis. The yield amounts to 99 %.

Workup

  1. temperatureThe whole is heated
  2. temperatureunder reflux for 3 days
  3. distillationwhile distilling off the water-benzene mixture
  4. customThe remaining benzenic solution is evaporated to dryness under reduced pressure
  5. customdried in vacuo to constant weight
  6. custom74.3 g of 4-cyclohexyl-1-morpholyl-cyclohex-1-ene are recovered
  7. customused without further purification for the next step of the synthesis

Sources & evidence

ORD record
ord-2bc61f74825f4de4973fabba62211059
Source dataset
uspto-grants-1976_08
Patent number
US03978044

Reaction notes

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