Dimethyl Sulfoxide → 1-(3-Cyanophenyl)piperazine

HRID 551290

Reaktionsgleichung

Reaktionsgleichung von HRID 551290
F[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[NH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.CS(C)=O>O>[C:5]([C:4]1[CH:3]=[C:2]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH:9]=[CH:8][CH:7]=1)#[N:6]

Komponenten

5

Edukt 3

HCID 679Dimethyl SulfoxideHCID 4837PiperazineHCID 678803-Fluorobenzonitrile

Produkt 1

HCID 114809021-(3-Cyanophenyl)piperazineAusbeute 143,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 3-fluorobenzonitrile (3.0 g, 25 mmol), piperazine (11.8 g, 137 mmol) and dimethylsulphoxide (20 ml) is heated at 100° C. for 48 hours under an atmosphere of nitrogen. The reaction mixture is then cooled, poured into water (200 ml) and the resultant precipitate collected. This solid is chromatographed on silica gel (dichloromethane) to give the title compound as a white solid (6.7 g). 1H NMR (DMSO, 500 MHz) δ7.15-7.40 (m, 4H), 3.28 (m, 3H), 3.12 (m, 1H), 2.80 (m, 1H), 2.59 (m, 3H).

Aufarbeitung

  1. temperatureThe reaction mixture is then cooled
  2. customthe resultant precipitate collected
  3. customThis solid is chromatographed on silica gel (dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-54a39dc3799e48f296756f3420669cff
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947684B2

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