Potassium Hydroxide → (E)-3-(4-{(E)-3-[4-(4-benzoyl-piperazin-1-yl)-phenyl]-3-oxo-propenyl}-phenyl)-acrylic acid

HRID 885862

Reaktionsgleichung

Reaktionsgleichung von HRID 885862
[C:1]([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:23])[CH3:22])=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:24]([C:26]1[CH:36]=[CH:35][C:29]([CH:30]=[CH:31][C:32]([OH:34])=[O:33])=[CH:28][CH:27]=1)=O.[OH-].[K+]>O1CCOCC1.CCO.O>[C:1]([N:9]1[CH2:10][CH2:11][N:12]([C:15]2[CH:16]=[CH:17][C:18]([C:21](=[O:23])/[CH:22]=[CH:24]/[C:26]3[CH:27]=[CH:28][C:29](/[CH:30]=[CH:31]/[C:32]([OH:34])=[O:33])=[CH:35][CH:36]=3)=[CH:19][CH:20]=2)[CH2:13][CH2:14]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 3

HCID 14797Potassium HydroxideHCID 980772-Propenoic acid, 3-(4-formylphenyl)-HCID 12451881-[4-(4-Benzoylpiperazin-1-yl)phenyl]ethanone

Produkt 1

HCID 67049914(E)-3-(4-{(E)-3-[4-(4-benzoyl-piperazin-1-yl)-phenyl]-3-oxo-propenyl}-phenyl)-acrylic acidAusbeute 31,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

1-[4-(4-Benzoyl-piperazin-1-yl)-phenyl]-ethanone (500 mg, 1.62 mmol) was dissolved in 1,4-dioxane (3 ml) and added to a stirred solution of 4-formylcinnamic acid (286 mg, 1.62 mmol) and 1.7 M KOH (1.9 ml) in EtOH (5 ml) and water (5 ml). The resulting mixture was stirred overnight at room temperature and then heated to 40° C. for 4 h. The reaction was then quenched with 10% HCl, the resulting precipitate was filtered and washed with EtOH. The resulting green solid was dried in vacuo to give 240 mg of (E)-3-(4-{(E)-3-[4-(4-benzoyl-piperazin-1-yl)-phenyl]-3-oxo-propenyl}-phenyl)-acrylic acid as its hydrochloride salt.

Aufarbeitung

  1. temperatureheated to 40° C. for 4 h
  2. customThe reaction was then quenched with 10% HCl
  3. filtrationthe resulting precipitate was filtered
  4. washwashed with EtOH
  5. customThe resulting green solid was dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-332750017d7d430f86dc44a2a672b1c1
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08242175B2

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