Sodium Iodide → HCID 67811489, Verbindung

HRID 923656Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 923656
Cl[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:7][CH2:6]1)=[O:4].[I-:16].[Na+]>CC(C)=O>[I:16][CH2:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:7][CH2:6]1)=[O:4]

Komponenten

4

Edukt 2

HCID 5238Sodium IodideHCID 2063649HCID 2063649, Verbindung

Produkt 1

HCID 67811489HCID 67811489, VerbindungAusbeute 75,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of ethyl 4-(2-chloroacetyl)piperazine-1-carboxylate (2.36 g, 10.06 mmol) and sodium iodide (3 g, 20.11 mmol) in acetone (45 mL) was stirred at room temperature for 24 h to give a suspension containing white solids. The solids were removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was extracted with CH2Cl2 and H2O. The organic layer then dried over MgSO4, filtered and concentrated to give ethyl 4-(2-iodoacetyl)piperazine-1-carboxylate (2.47 g, 75% yield). C9H151N2O3; brown oil; IR vmax (neat) 2981, 2927, 2864, 1697, 1642, 1464, 1434, 1385, 1286, 1232, 1133, 1073, 1030, 989, 767 cm−1; 1H NMR (400 MHz, CDCl3) δ 4.14 (2H, q, J=7.0 Hz), 3.75 (2H, s), 3.58 (4H, m), 3.43 (4H, m), 1.26 (3H, t, J=7.0 Hz); 13C NMR (100 MHz, CDCl3) δ 166.6, 155.1, 61.8, 47.0, 43.1 (2×), 42.0 (2×), 14.7; ESI-HRMS calcd for C9H161N2O3: 327.0206. found: m/z 327.0215 [M+H]+.

Aufarbeitung

  1. customto give a suspension
  2. additioncontaining white solids
  3. customThe solids were removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. extractionThe residue was extracted with CH2Cl2 and H2O
  6. dry with materialThe organic layer then dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-593a04203fe04e6b9bb369ad8e7051e7
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09278982B2

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