Water → HCID 57117243, compound

HRID 1700346Notes

Reaction equation

HRID 1700346 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].[NH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.[C:23]1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1>[C:2]([C:3](=[CH:23][C:19]1[CH:18]=[N:17][CH:22]=[CH:21][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

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 8082PiperidineHCID 53935748HCID 53935748, compound

Product 1

HCID 57117243HCID 57117243, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

516 mg (2.37 mmol) of 3-oxo-N-(3-phenyl-2-propene-1-yl)butyramide, 0.255 ml (2.70 mmol) of 3-pyridylaldehyde and 0.06 ml (0.61 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. After washing 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-(pyridine-3-yl)-N-(3-phenyl-2-propene-1-yl)acrylamide. 20 ml of 2-propanol and 365 mg (2.37 mmol) of 2-cyanoethyl 3-aminocrotonate were added to the product, and they were heated at 80° C. under stirring overnight. 2-Propanol was evaporated under reduced pressure, and the residue was purified by the silica gel chromatography (chloroform/methanol=50/1) to obtain the title compound.

Workup

  1. customwas removed
  2. additionEthyl acetate was added to the reaction mixture
  3. washAfter washing with a saturated aqueous sodium hydrogencarbonate solution
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-897d2ec5094c4d0997d2bd6935e9b287
Source dataset
uspto-grants-2002_02
Patent number
US06350762B1

Reaction notes

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