Diisopropylethylamine → HCID 67500566, Verbindung

HRID 1920202Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1920202
[Cl:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH:3]1[NH:8][P:9](=[O:16])([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12].Cl[C:18]1[CH:23]=[CH:22][N:21]=[CH:20][C:19]=1[N+:24]([O-:26])=[O:25].CCN(C(C)C)C(C)C>C(O)(C)C>[Cl:1][CH:2]1[CH2:7][CH2:6][N:5]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][C:19]=2[N+:24]([O-:26])=[O:25])[CH2:4][CH:3]1[NH:8][P:9](=[O:16])([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 27357814-Chloro-3-nitropyridineHCID 67500859Diethyl 4-chloropiperidin-3-ylphosphoramidate

Produkt 1

HCID 67500566HCID 67500566, VerbindungAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of diethyl 4-chloropiperidin-3-ylphosphoramidate (1.0 equiv.) in isopropyl alcohol (0.1M) was added 4-chloro-3-nitropyridine (2.0 equiv.) and DIEA (1.1 equiv.). The reaction was heated to 70° C. for 18 h, then quenched with water and extracted with ethyl acetate. The organics were dried and concentrated under vacuo. The crude was purified via ISCO (ethyl acetate and hexanes then 10% methanol in DCM) to yield diethyl 4-chloro-1-(3-nitropyridin-4-yl)piperidin-3-ylphosphoramidate in 69% yield. LCMS (m/z): 393.1 (MH+), Rt=2.01 min.

Aufarbeitung

  1. customquenched with water
  2. extractionextracted with ethyl acetate
  3. customThe organics were dried
  4. concentrationconcentrated under vacuo
  5. customThe crude was purified via ISCO (ethyl acetate and hexanes

Quellen und Nachweise

ORD-Eintrag
ord-f633989b41a741c6a62a939ec412b140
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08168794B2

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