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Cyclopropanecarboxylic acid → cyclopropyl-{4-[3-(1-methyl-1H-benzoimidazol-2-yl)-phenyl]-piperazin-1-yl}-methanone

HRID 2047374
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2047374
[CH:1]1([C:4]([OH:6])=O)[CH2:3][CH2:2]1.C1N=CN(C(N2C=NC=C2)=O)C=1.Cl.Cl.[CH3:21][N:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[N:24]=[C:23]1[C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([N:37]2[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]2)[CH:32]=1>C(#N)C>[CH:1]1([C:4]([N:40]2[CH2:41][CH2:42][N:37]([C:33]3[CH:34]=[CH:35][CH:36]=[C:31]([C:23]4[N:22]([CH3:21])[C:26]5[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=5[N:24]=4)[CH:32]=3)[CH2:38][CH2:39]2)=[O:6])[CH2:3][CH2:2]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 15655Cyclopropanecarboxylic acidHCID 682631,1'-CarbonyldiimidazoleHCID 686704331-Methyl-2-(3-piperazin-1-yl-phenyl)-1H-benzoimidazole dihydrochloride

Produkt 1

HCID 68671116cyclopropyl-{4-[3-(1-methyl-1H-benzoimidazol-2-yl)-phenyl]-piperazin-1-yl}-methanoneAusbeute 85,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342
Acetonitrile
Lösungsmittel

Versuchsvorschrift

To a solution of cyclopropanecarboxylic acid (0.06 g, 0.68 mmol) in acetonitrile (8 mL) was added CDI (0.11 g, 0.68 mmol) and the resulting suspension was stirred at room temperature for 5 h. 1-Methyl-2-(3-piperazin-1-yl-phenyl)-1H-benzoimidazole dihydrochloride (0.20 g, 0.55 mmol) was added and the resulting solution heated at 65° C. overnight. The reaction was then cooled to room temperature, the solvent removed under reduced pressure. The crude product was redissolved in dichloromethane (15 mL) and washed with saturated NaHCO3 solution (2×3 mL) The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (eluent: cyclohexane:EtOAc, gradient from 100% cyclohexane to 100% ethyl acetate) to afford 0.17 g (85%) of the title compound.

Aufarbeitung

  1. temperaturethe resulting solution heated at 65° C. overnight
  2. temperatureThe reaction was then cooled to room temperature
  3. customthe solvent removed under reduced pressure
  4. dissolutionThe crude product was redissolved in dichloromethane (15 mL)
  5. washwashed with saturated NaHCO3 solution (2×3 mL) The organic layer
  6. dry with materialwas dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash chromatography (eluent: cyclohexane:EtOAc, gradient from 100% cyclohexane to 100% ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-1c01f9252fe94edeb073a4b3f83cbbce
Quelldatensatz
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08592463B2

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