N-[2-(4-benzyl-piperazin-1-yl)-2-oxo-ethyl]-4-phenoxy-benzamide → N-(2-Oxo-2-piperazin-1-yl-ethyl)-4-phenoxy-benzamide

HRID 1178025

Reaktionsgleichung

Reaktionsgleichung von HRID 1178025
C([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:32])[CH2:15][NH:16][C:17](=[O:31])[C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:20][CH:19]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[O:32]=[C:14]([N:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)[CH2:15][NH:16][C:17](=[O:31])[C:18]1[CH:19]=[CH:20][C:21]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:22][CH:23]=1

Komponenten

5

Edukt 2

HCID 27671405N-[2-(4-benzyl-piperazin-1-yl)-2-oxo-ethyl]-4-phenoxy-benzamideHCID 178418361HCID 178418361, Verbindung2×

Produkt 1

HCID 59559582N-(2-Oxo-2-piperazin-1-yl-ethyl)-4-phenoxy-benzamideAusbeute 100,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

Under an inert atmosphere, 10% Pd/C (111 mg) was added to a stirred solution of N-[2-(4-benzyl-piperazin-1-yl)-2-oxo-ethyl]-4-phenoxy-benzamide (490 mg, 1.14 mmol) in MeOH (90 mL). Hydrogen gas was then passed into the reaction mixture by means of a hydrogen filled bladder and the mixture was stirred at room temperature overnight. The mixture was filtered over celite and the celite was washed with MeOH. The filtrate was collected and concentrated under reduced pressure to afford 390 mg (quantitative yield) of N-(2-Oxo-2-piperazin-1-yl-ethyl)-4-phenoxy-benzamide as a solid. LC-MS purity: 88.65, 1H NMR (CDCl3): δ 7.8 (d, 2H), 7.38 (m, 2H), 7.26 (bs, 1H), 7.18 (tt, 1H), 7.08-7.0 (m, 4H), 4.24 (d, 2H), 3.66 (t, 2H), 3.5 (s, 1H), 3.44 (t, 2H), 2.9 (q, 4H), 2.5-2.6 (m, 1H).

Aufarbeitung

  1. filtrationThe mixture was filtered over celite
  2. washthe celite was washed with MeOH
  3. customThe filtrate was collected
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7ad2e13fe3054ed9926943099dfda10d
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842696B2

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