1-Phenylpiperazine → 3-[4-(4-Chlorophenyl)-2-(4-phenyl-l-piperazinyl)-5-oxazolyl]propionic acid

HRID 350743Notizen

Reaktionsgleichung

Cl[C:2]1[O:3][C:4]([CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[N:6]=1.[C:19]1([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CN(C)C=O>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]2[N:6]=[C:2]([N:28]3[CH2:29][CH2:30][N:25]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:26][CH2:27]3)[O:3][C:4]=2[CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:8][CH:9]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

A mixture of 3-[2-chloro-4-(4-chlorophenyl)-5-oxazolyl]propionic acid (1.0 g), 1-phenylpiperazine (2.27 g), potassium carbonate (2.42 g) and N,N-dimethylformamide (20 mL) was stirred at 100° C. for 3 hrs. The reaction mixture was poured into aqueous ammonium chloride solution and the mixture was extracted with ethyl acetate, washed with water, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography and 3-[4-(4-chlorophenyl)-2-(4-phenyl-l-piperazinyl)-5-oxazolyl]propionic acid (0.76 g, yield 53%) was obtained as a powder from a fraction eluted with ethyl acetate-chloroform-methanol (10:10:1, volume ratio). Recrystallization from ethyl acetate gave colorless prism crystals. melting point: 177–178° C.

Aufarbeitung

extractionthe mixture was extracted with ethyl acetate
washwashed with water
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated
customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag: ord-c70f9d88ad9b4b9e981f5d7c8d433fa1
Quelldatensatz: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07183276B2

Notizen zur Reaktion

Wird geladen…