반응 #416583

반응 방정식

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

N-(8-quinolyl)piperazine

sodium carbonate

sodium iodide

→

4-(4-(2-(4-(8-Quinolyl)piperazinyl)ethyl)phenyl)-2-aminothiazole

용매

ethanol

ethyl acetate water

반응 조건

후처리

1. 1
   기타To a 35 ml round-bottomed flask equipped with condenser and N2 inlet
2. 2
   온도The reaction was heated
3. 3
   온도at reflux for 25 hours
4. 4
   온도cooled
5. 5
   기타The layers were separated
6. 6
   건조the ethyl acetate layer dried
7. 7
   기타evaporated
8. 8
   기타The residue was chromatographed on silica gel
9. 9
   기타precipitated with a solution of hydrochloride in ether
10. 10
    기타to afford a crystalline solid, m.p. >225° C., 277 mg (27%)

실험 절차

To a 35 ml round-bottomed flask equipped with condenser and N2 inlet were added 0.746 g (2.34 mmol) of 4-(4-(2-chloroethyl)phenyl-2-aminothiazole hydrobromide, 0.50 g (2.34 mmol) of N-(8-quinolyl)piperazine (prepared from 8-aminoquinoline by reaction with diethanolamine in hydrobromide at 200° C.), 0.621 g (5.86 mmol) of sodium carbonate, 50 mg of sodium iodide, and 10 ml of ethanol. The reaction was heated at reflux for 25 hours, cooled, and the reaction mixture taken up in ethyl acetate/water. The layers were separated, the ethyl acetate layer dried and evaporated. The residue was chromatographed on silica gel using chloroform/methanol as eluent and the product fractions combined in methanol and precipitated with a solution of hydrochloride in ether. The precipitate was stirred with ether/methanol to afford a crystalline solid, m.p. >225° C., 277 mg (27%). NMR (free base in CDCl3): 2.8 (m, 8H), 3.5 (m, 4H), 7.0-8.2 (m, 11H).

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