4-Fluorobenzoic Acid → N-{2-[4-(4-fluoro-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-4-phenoxy-benzamide

HRID 1178033Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1178033
CCN(C(C)C)C(C)C.[F:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.Cl.[O:42]=[C:43]([N:61]1[CH2:66][CH2:65][NH:64][CH2:63][CH2:62]1)[CH2:44][NH:45][C:46](=[O:60])[C:47]1[CH:52]=[CH:51][C:50]([O:53][C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)=[CH:49][CH:48]=1>CN(C=O)C.O>[F:10][C:11]1[CH:12]=[CH:13][C:14]([C:15]([N:64]2[CH2:65][CH2:66][N:61]([C:43](=[O:42])[CH2:44][NH:45][C:46](=[O:60])[C:47]3[CH:48]=[CH:49][C:50]([O:53][C:54]4[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=4)=[CH:51][CH:52]=3)[CH2:62][CH2:63]2)=[O:17])=[CH:18][CH:19]=1

Komponenten

8

Edukt 5

HCID 99734-Fluorobenzoic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 66953134N-(2-Oxo-2-piperazin-1-yl-ethyl)-4-phenoxy-benzamide hydrochloride

Produkt 1

HCID 59559676N-{2-[4-(4-fluoro-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-4-phenoxy-benzamideAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

DIPEA (0.138 mL, 0.80 mmol) was added drop wise to 4-fluorobenzoic acid (44 mg, 0.32 mmol) in DMF (5 mL). EDCI (127 mg, 0.67 mmol) and HOBT (43 mg, 0.32 mmol) were added consecutively and, after 10 mins, N-(2-oxo-2-piperazin-1-yl-ethyl)-4-phenoxy-benzamide hydrochloride (100 mg, 0.27 mmol) was added and the resulting mixture was stirred at room temperature overnight. Water was then added, and the product was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to afford the crude product. Purification using column chromatography (silica gel of mesh size of 60-120 using 70:30 EtOAc:hexane as eluent) afforded N-{2-[4-(4-fluoro-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-4-phenoxy-benzamide in 49% yield. LC-MS purity: 97%, 1H NMR (CDCl3): δ 7.8 (d, 2H), 7.4 (m, 4H), 7.2 (m, 4H), 7.1 (m, 4H), 4.3 (s, 2H), 3.6 (m, 8H).

Aufarbeitung

  1. extractionthe product was extracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto afford the crude product
  6. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-304002b270254ed687072eccb590cdb2
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842696B2

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