Sodium Iodide → N,N-Diethyl-N-(2-{[6-fluoro-9-(4-fluorobenzyl)-9H-carbazol-4-yl]oxy}ethyl)amine

HRID 1057633Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1057633
[F:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)[C:10]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:23])[C:5]2=1.Cl.[CH2:25]([N:27]([CH2:31][CH3:32])[CH2:28][CH2:29]Cl)[CH3:26].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C=O)C>[CH2:25]([N:27]([CH2:31][CH3:32])[CH2:28][CH2:29][O:23][C:6]1[C:5]2[C:4]3[C:12](=[CH:13][CH:14]=[C:2]([F:1])[CH:3]=3)[N:11]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:10]=2[CH:9]=[CH:8][CH:7]=1)[CH3:26]

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 186716846-Fluoro-9-(4-fluorobenzyl)-9H-carbazol-4-ol

Produkt 1

HCID 18671674N,N-Diethyl-N-(2-{[6-fluoro-9-(4-fluorobenzyl)-9H-carbazol-4-yl]oxy}ethyl)amineAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

6-Fluoro-9-(4-fluorobenzyl)-9H-carbazol-4-ol (0.0584 g, 0.19 mmol), 2-diethylaminoethylchloride hydrochloride (0.0593 g, 0.35 mmol), potassium carbonate (0.0926 g, 0.63 mmol), sodium iodide (0.0061 g, 0.041 mmol) and DMF (2 mL) are heated at 85° C. for 3 h. After the mixture had cooled, it is partitioned between water and ethyl acetate. The combined organic layers are dried over magnesium sulfate and concentrated to an oil. The oil is chromatographed on silica gel (50 mL) using methanol/dichloromethane (1/99) to give 0.0471 g (61%) of the title compound; mp 75-76° C.; MS (ESI+) for C25H26F2N2O m/z 409.3 (M+H)+; IR (drift) 1585, 1507, 1481, 1461, 1343, 1269, 1221, 1159, 1145, 871, 820, 799, 776, 739, 712 cm−1; 1H NMR (CDCl3) δ1.14, 2.73, 3.10, 4.33, 5.44, 6.69, 6.93, 7.04-7.18, 7.36, 8.03. Anal. Calcd for C25H26F2N2O: C, 73.51; H, 6.41; N, 6.86. Found:C, 73.30; H, 6.59; N, 6.77.

Aufarbeitung

  1. temperatureAfter the mixture had cooled
  2. customit is partitioned between water and ethyl acetate
  3. dry with materialThe combined organic layers are dried over magnesium sulfate
  4. concentrationconcentrated to an oil
  5. customThe oil is chromatographed on silica gel (50 mL)

Quellen und Nachweise

ORD-Eintrag
ord-64237b9df4584a5a88f63fa44e21e0e1
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06514968B1

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