Dimethyl Sulfoxide → 1-[5-(4-Chlorophenyl)pyridin-2-yl]-4-(propan-2-yl)piperazine

HRID 80867

Reaktionsgleichung

Reaktionsgleichung von HRID 80867
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)=[CH:4][N:3]=1.CS(C)=O.[CH:19]([N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)([CH3:21])[CH3:20]>O>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([N:25]3[CH2:26][CH2:27][N:22]([CH:19]([CH3:21])[CH3:20])[CH2:23][CH2:24]3)=[N:3][CH:4]=2)=[CH:9][CH:10]=1

Komponenten

5

Edukt 3

HCID 679Dimethyl SulfoxideHCID 780131-IsopropylpiperazineHCID 100365542-Chloro-5-(4-chlorophenyl)pyridine

Produkt 1

HCID 159513151-[5-(4-Chlorophenyl)pyridin-2-yl]-4-(propan-2-yl)piperazineAusbeute 85,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 2-chloro-5-(4-chlorophenyl)pyridine (500 mg, 2.23 mmol), DMSO (2.0 mL) and 1-isopropylpiperazine (3 mL, 23.4 mmol) was stirred and heated on a 100° C. oil-bath overnight. The reaction mixture was poured into water (75 mL), and the solid was isolated by filtration, washed with water and dried. The crude product was purified by column chromatography on silica gel (Kiselgel 60, mesh 0.040-0.63) eluting with a mixture of ethyl acetate and methanol (4:1). Collecting the proper fractions afforded 600 mg (85%) of 1-[5-(4-chlorophenyl)pyridin-2-yl]-4-isopropylpiperazine.

Aufarbeitung

  1. customthe solid was isolated by filtration
  2. washwashed with water
  3. customdried
  4. customThe crude product was purified by column chromatography on silica gel (Kiselgel 60, mesh 0.040-0.63)
  5. washeluting with a mixture of ethyl acetate and methanol (4:1)
  6. customCollecting the proper fractions

Quellen und Nachweise

ORD-Eintrag
ord-aa31204f69794e3a9f0466e3bad627a1
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846677B2

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