Morpholine → 4-[2-(Thiophen-2-yl)ethenyl]morpholine

HRID 1741615Notes

Reaction equation

HRID 1741615 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH:7]=O.[NH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C[O-].[Na+]>C1(C)C=CC=CC=1.O>[O:12]1[CH2:13][CH2:14][N:9]([CH:7]=[CH:6][C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)[CH2:10][CH2:11]1

Participants

7

Reactant 4

HCID 8083MorpholineHCID 521998p-Toluenesulfonic acid monohydrateHCID 6430722thienylethanalHCID 10942334Sodium Methoxide

Product 1

HCID 540174394-[2-(Thiophen-2-yl)ethenyl]morpholine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 1.5 g of 2-thienylacetaldehyde, 1.4 mL of morpholine, and 0.012 g of p-toluenesulfonic acid hydrate in 7.5 mL of toluene is heated at reflux under a Dean-Stark Trap with azeotropic removal of water for 3 hours. The solution is cooled, neutralized by the addition of solid sodium methoxide, and concentrated in vacuo. The residue is taken up in toluene, filtered, and concentrated in vacuo to afford the desired enamine as an oil.

Workup

  1. temperatureis heated
  2. temperatureThe solution is cooled
  3. concentrationconcentrated in vacuo
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4656e1e58d284c8c94efb3e0cb10f85c
Source dataset
uspto-grants-1994_08
Patent number
US05334576

Reaction notes

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