Ethyl Acetate → 2-[4-(1-Benzothien-2-ylmethyl)-1-piperazinyl]benzonitrile

HRID 2377674

Reaktionsgleichung

Reaktionsgleichung von HRID 2377674
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH2:10]O.CS(OS(C)(=O)=O)(=O)=O.CC(=O)OCC.[N:27]1([C:33]2[CH:40]=[CH:39][CH:38]=[CH:37][C:34]=2[C:35]#[N:36])[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1>C(Cl)Cl>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH2:10][N:30]1[CH2:29][CH2:28][N:27]([C:33]2[CH:40]=[CH:39][CH:38]=[CH:37][C:34]=2[C:35]#[N:36])[CH2:32][CH2:31]1

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 81560Methanesulfonic anhydrideHCID 2735875N-(2-Cyanophenyl)piperazineHCID 27763352-(Hydroxymethyl)benzo[b]thiophene

Produkt 1

HCID 99969482-[4-(1-Benzothien-2-ylmethyl)-1-piperazinyl]benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The product from Example 8A (150 mg 0.9 mmol), methane sulfonic anhydride (159 mg, 0.9 mmol), and D1 EA (475 μL 2.7 mmol) were combined. After stirring, 2-(1-piperazinyl)benzonitrile (181 mg, 1.0 mmol) in 2 ml DCM was also combined and stirred at room temperature for 18 hours. The mixture was concentrated and the residue was taken up in hot methanol. The methanol was filtered and the filter cake washed with cold methanol to provide the title compound. 1H NMR (300 MHz, CDCl3) δ 2.69 (m, 4H) 3.04 (s, 4H) 3.76 (m, 4H) 3.86 (s, 1H) 6.74 (m, 2H) 7.29 (m, 3H) 7.75 (m, 1H); (ESI) m/z 334 (M+H)+.

Aufarbeitung

  1. stirringstirred at room temperature for 18 hours
  2. concentrationThe mixture was concentrated
  3. filtrationThe methanol was filtered
  4. washthe filter cake washed with cold methanol

Quellen und Nachweise

ORD-Eintrag
ord-c9a658dc3dd743c4a7da7ed15e88db60
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07470691B2

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