Acetic Acid → 2-acetyl-3-(3-chlorophenyl)-N-(3-phenyl-2-propene-1-yl)acrylamide

HRID 1727878Notes

Reaction equation

HRID 1727878 reaction equation
[O:1]=[C:2]([CH3:15])[CH2:3][CH2:4][N-:5][CH2:6][CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Cl:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=O.N1CCCCC1.C(O)(=[O:33])C>CC(O)C>[C:2]([C:3](=[CH:20][C:19]1[CH:22]=[CH:23][CH:24]=[C:17]([Cl:16])[CH:18]=1)[C:4]([NH:5][CH2:6][CH:7]=[CH:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:33])(=[O:1])[CH3:15]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 114773-ChlorobenzaldehydeHCID 866191923-oxo-N-(3-phenyl-2-propen-1-yl)butylamide

Product 1

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

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

30.0 mg (1.38 mmol) of 3-oxo-N-(3-phenyl-2-propen-1-yl)butylamide and 194 mg (1.38 mmol) of 3-chlorobenzaldehyde were dissolved in 20 ml of 2-propanol. 4.14 mg (0.0690 mmol) of piperidine and 5.67 mg (0.0690 mmol) of acetic acid were added thereto and stirred at room temperature for 2 days. After the solvent was evaporated under reduced pressure, ethyl acetate was added to the reaction mixture. After washing with 1 N hydrochloric acid and then with saturated aqueous sodium hydrogencarbonate solution, the organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1) to obtain the title compound.

Workup

  1. customAfter the solvent was evaporated under reduced pressure, ethyl acetate
  2. additionwas added to the reaction mixture
  3. washAfter washing with 1 N hydrochloric acid
  4. dry with materialwith saturated aqueous sodium hydrogencarbonate solution, the organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-ed93f60295b64cfbafa4a8cd7f2ecab5
Source dataset
uspto-grants-2009_02
Patent number
US07494989B2

Reaction notes

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