Potassium Iodide → 1-{4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl}-1H-benzimidazole

HRID 1482581Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1482581
Cl[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[CH:7]1.[N:15]1[CH:20]=[CH:19][CH:18]=[N:17][C:16]=1[N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C(N(C(C)C)CC)(C)C.[I-].[K+]>C(#N)C>[N:15]1[CH:20]=[CH:19][CH:18]=[N:17][C:16]=1[N:21]1[CH2:26][CH2:25][N:24]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[N:8]=[CH:7]2)[CH2:23][CH2:22]1

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 81531DiisopropylethylamineHCID 887471-(2-Pyrimidinyl)piperazineHCID 583170Benzimidazole, 1-(4-chlorobutyl)-

Produkt 1

HCID 98191481-{4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl}-1H-benzimidazoleAusbeute 60,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

1-(4-chlorobutyl)-1H-benzimidazole (7.51 g, 0.036 mol) was dissolved into 100 ml of acetonitrile, 4-(2-pyrimidinyl) piperazine (4.9 g, 0.03 mol), diisopropylethylamine (15.5 g, 0.12 mol) and potassium iodide (5.0 g, 0.03 mol) were respectively added. The mixture was stirred for 10 min at ambient temperature, and then heated and refluxed to react for 20 hours. The mixture was cooled down to ambient temperature and filtered. The filtrate was concentrated to produce oily products, and treated by chromatography with neutral Al2O3, eluted with dichloromethane/methanol mixture to produce 6.1 g compound (I-14) with a yield of 60.1%. ESI-MS [M+H]+: m/z 337.2.

Aufarbeitung

  1. additionwere respectively added
  2. temperatureheated
  3. temperaturerefluxed
  4. customto react for 20 hours
  5. temperatureThe mixture was cooled down to ambient temperature
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. customto produce oily products
  9. additiontreated by chromatography with neutral Al2O3
  10. washeluted with dichloromethane/methanol mixture

Quellen und Nachweise

ORD-Eintrag
ord-8566a497b24d47ceb8afa8c42df5029d
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09415047B2

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