Diisopropylamine → N-(3-nitrophenyl)-2-(4-pyridin-2-ylpiperazin-1-yl)acetamide

HRID 490215Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 490215
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.C(NC(C)C)(C)C.Cl[CH2:21][C:22]([NH:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([N+:31]([O-:33])=[O:32])[CH:26]=1)=[O:23]>C1(C)C=CC=CC=1>[N+:31]([C:27]1[CH:26]=[C:25]([NH:24][C:22](=[O:23])[CH2:21][N:10]2[CH2:9][CH2:8][N:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[CH2:12][CH2:11]2)[CH:30]=[CH:29][CH:28]=1)([O-:33])=[O:32]

Komponenten

5

Edukt 3

HCID 7912DiisopropylamineHCID 944591-(2-Pyridyl)piperazineHCID 5320662-chloro-N-(3-nitrophenyl)acetamide

Produkt 1

HCID 8547156N-(3-nitrophenyl)-2-(4-pyridin-2-ylpiperazin-1-yl)acetamideAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

1-(2-pyridinyl)piperazine (0.65 mL, 4.3 mmol, Aldrich) and N,N-diisopropylamine (5.0 mL) in toluene (20 mL) were treated with 2-chloro-N-(3-nitrophenyl)acetamide (750 mg, 3.49 mmol, Lancaster) and heated to 60° C. for 18 hours. The mixture was allowed to cool to room temperature, transferred to a separatory funnel and washed with saturated aqueous sodium bicarbonate. The organic phase was dried (sodium sulfate), filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (elution with 25% ethyl acetate:hexanes) to provide 900 mg (76% yield) of the title compound as a tan solid. 1H NMR (300 MHz, DMSO-d6) δ 2.62 (m, 4H), 3.24 (s, 2H), 3.56 (m, 4H), 6.63 (ddd, 1H, J=7.1, 4.7, 0.7 Hz), 6.83 (d, 1H, J=8.8 Hz), 7.52 (ddd, 1H, J=8.5, 7.1, 2.0), 7.61 (dd, 1H, J=8.5, 8.5 Hz), 7.92 (ddd, 1H, J=8.1, 2.4, 1.0 Hz), 8.04 (ddd, 1H, J=8.5, 2.4, 1.0 Hz), 8.11 (ddd, 1H, J=4.8, 1.7, 0.7 Hz), 8.70 (dd, 1H, J=2.0, 2.0 Hz), 10.27 (br s, 1H); MS (DCI/NH3) m/e 342 (M+H)+; Anal. calcd for C17H19N5O3: C, 59.81; H, 5.61; N, 20.52. Found: C, 59.61; H, 5.55; N, 20.23.

Aufarbeitung

  1. temperatureto cool to room temperature
  2. customtransferred to a separatory funnel
  3. washwashed with saturated aqueous sodium bicarbonate
  4. dry with materialThe organic phase was dried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under reduced pressure
  7. customThe residue was purified by flash column chromatography on silica gel (elution with 25% ethyl acetate:hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-802be5284a0e40f6865b674051c9a82f
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07528134B2

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