Reaktion #416584

Reaktionsgleichung

4-(4-(2-chloroethyl)phenyl)-2-methylaminothiazole hydrobromide

N-(1-naphthyl)piperazine

diisopropylethylamine

sodium carbonate

sodium iodide

→

4-(4-(2-(4-(1-Naphthyl)piperazinyl)ethyl)phenyl)-2-methylaminothiazole

Lösungsmittel

methylene chloride

methylisobutylketone

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeTo a 125 ml round-bottomed flask equipped with condenser and N2 inlet
2. 2
   TemperaturThe reaction was heated
3. 3
   Temperaturat reflux for 4 days
4. 4
   Temperaturcooled
5. 5
   Filtrationthe precipitate filtered
6. 6
   Sonstigethe filtrate evaporated
7. 7
   Sonstigechromatographed on silica gel
8. 8
   Sonstigeto give an oil
9. 9
   Sonstigeprecipitated by addition of methylene chloride saturated with hydrochloride
10. 10
    Filtrationthe precipitate filtered
11. 11
    Waschenwashed with ether
12. 12
    Sonstigedried
13. 13
    Sonstigeto give a white solid, m.p. 272°-273° C., 2.37 g (63%)

Vorschrift

To a 125 ml round-bottomed flask equipped with condenser and N2 inlet were added 2.50 g (7.5 mmol) of 4-(4-(2-chloroethyl)phenyl)-2-methylaminothiazole hydrobromide, 1.59 g (7.5 mmol) of N-(1-naphthyl)piperazine, 1.31 ml (7.5 mmol) of diisopropylethylamine, 1.59 g (15 mmol) of sodium carbonate, 5 mg of sodium iodide, and 50 ml of methylisobutylketone. The reaction was heated at reflux for 4 days, cooled, and the precipitate filtered, and the filtrate evaporated. The residue was taken up in methylene chloride and chromatographed on silica gel using methylene chloride/ethyl acetate as eluent to give an oil. The oil was taken up in methylene chloride, precipitated by addition of methylene chloride saturated with hydrochloride, and the precipitate filtered, washed with ether, and dried to give a white solid, m.p. 272°-273° C., 2.37 g (63%).

Quelle