p-Toluenesulfonic acid → 2-acetyl-3-(4-cyanophenyl)-N-(3-phenyl-2-propene-1-yl)acrylamide

HRID 1700345Notes

Reaction equation

HRID 1700345 reaction equation
[O:1]=[C:2]([CH3:16])[CH2:3][C:4]([NH:6][CH2:7][CH:8]=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:5].[C:17]([C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1)#[N:18].N1CCCCC1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1.O>[C:2]([C:3](=[CH:23][C:22]1[CH:25]=[CH:26][C:19]([C:17]#[N:18])=[CH:20][CH:21]=1)[C:4]([NH:6][CH2:7][CH:8]=[CH:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:5])(=[O:1])[CH3:16]

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8082PiperidineHCID 660424-CyanobenzaldehydeHCID 53935748HCID 53935748, compound

Product 1

HCID 538596572-acetyl-3-(4-cyanophenyl)-N-(3-phenyl-2-propene-1-yl)acrylamide

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

600 mg (2.76 mmol) of 3-oxo-N-(3-phenyl-2-propene-1-yl)butyramide, 362 mg (2.76 mmol) of 4-cyanobenzaldehyde and 23.5 mg (0.276 mmol) of piperidine were heated under reflux in the presence of a catalytic amount of p-toluenesulfonic acid in 30 ml of benzene for 6 hours while water was removed. Benzene was evaporated under reduced pressure. Ethyl acetate was added to the reaction mixture. After washing with 1 N hydrochloric acid and then with a saturated aqueous sodium hydrogencarbonate solution, the organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=5/1) to obtain the title compound.

Workup

  1. customwas removed
  2. customBenzene was evaporated under reduced pressure
  3. additionEthyl acetate was added to the reaction mixture
  4. washAfter washing with 1 N hydrochloric acid
  5. dry with materialwith a saturated aqueous sodium hydrogencarbonate solution, the organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-6a0df87db22643e885edde25c9c99ce7
Source dataset
uspto-grants-2002_02
Patent number
US06350762B1

Reaction notes

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