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

HRID 1700353Notes

Reaction equation

HRID 1700353 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].[Cl:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH:21]=O.N1CCCCC1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1.O>[C:2]([C:3](=[CH:21][C:20]1[CH:23]=[CH:24][CH:25]=[C:18]([Cl:17])[CH:19]=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 114773-ChlorobenzaldehydeHCID 53935748HCID 53935748, compound

Product 1

HCID 541391202-acetyl-3-(3-chlorophenyl)-N-(3-phenyl-2-propene-1-yl)acrylamide

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

569 mg (2.62 mmol) of 3-oxo-N-(3-phenyl-2-propene-1-yl)butyramide, 0.3 ml (2.65 mmol) of 3-chlorobenzaldehyde and 0.03 ml (0.34 mmol) of piperidine were heated under reflux in the presence of a catalytic amount of p-toluenesulfonic acid in 30 ml of benzene overnight while water was removed. Ethyl acetate was added to the reaction mixture, and the product was washed 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 to obtain 2-acetyl-3-(3-chlorophenyl)-N-(3-phenyl-2-propene-1-yl)acrylamide. 20 ml of 2-propanol and 260 mg (2.62 mmol) of 4-amino-3-pentene-2-on were added to the product, and they were heated at 80° C. under stirring for 3 days. 2-Propanol was evaporated under reduced pressure, and the residue was purified by the silica gel chromatography (ethyl acetate) to obtain the title compound.

Workup

  1. customwas removed
  2. additionEthyl acetate was added to the reaction mixture
  3. washthe product was washed with 1 N hydrochloric acid
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-07fa269aefbc4de799fa3b5d1c21da6e
Source dataset
uspto-grants-2002_02
Patent number
US06350762B1

Reaction notes

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