p-Toluenesulfonic acid → HCID 54137441, compound

HRID 1700342Notes

Reaction equation

HRID 1700342 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:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH:22]=O)#[N:18].N1CCCCC1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1.O>[C:2]([C:3](=[CH:22][C:21]1[CH:24]=[CH:25][CH:26]=[C:19]([C:17]#[N:18])[CH:20]=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 90670m-FormylbenzonitrileHCID 53935748HCID 53935748, compound

Product 1

HCID 54137441HCID 54137441, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

541 mg (2.49 mmol) of 3-oxo-N-(3-phenyl-2-propene-1-yl)butyramide, 328 mg (2.50 mmol) of 3-cyanobenzaldehyde and 0.2 ml (2.02 mmol) of piperidine were heated under reflux in the presence of a catalytic amount of p-toluene Sulfonic acid in 30 ml of benzene overnight while water was removed. Ethyl acetate was added to the reaction mixture, which was washed with 2 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-cyanophenyl)-N-(3-phenyl-2-propene-1-yl) acrylamide. This product was heated together with 387 mg (2.5 1 mmol) of 2-cyanoethyl 3-aminocrotonate at 80° C. under stirring in 20 ml of 2-propanol for four days. 2-Propanol was evaporated under reduced pressure. The residue was purified by the silica gel chromatography (chloroform/methanol=100/1) to obtain the title compound.

Workup

  1. customwas removed
  2. additionEthyl acetate was added to the reaction mixture, which
  3. washwas washed with 2 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-f7aa0c9815a9430881f2d00e508af5d1
Source dataset
uspto-grants-2002_02
Patent number
US06350762B1

Reaction notes

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