Reaktion #416600

Reaktionsgleichung

2-methylthiazole hydrobromide

sodium iodide

diisopropylethyl amine

sodium carbonate

N-benzisothiazolylpiperazine

→

4-(4-(4-(4-(3-Benzisothiazolyl)piperazinyl)butyl)-phenyl)-2-methylthiazole

Lösungsmittel

methylene chloride

methylisobutyl ketone

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeTo a 100 ml round-bottomed flask equipped with condenser and N2 inlet
2. 2
   TemperaturThe reaction was refluxed 31 hours
3. 3
   Temperaturcooled
4. 4
   Filtrationfiltered
5. 5
   Sonstigethe filtrate evaporated
6. 6
   SonstigeThe residue was chromatographed on silica gel
7. 7
   Sonstigeto afford an oil, which
8. 8
   Sonstigeprecipitated by addition of ether saturated with HCl
9. 9
   FiltrationThe solid was filtered
10. 10
    Waschenwashed with ether
11. 11
    Sonstigedried briefly
12. 12
    Waschenwashed with a minimal amount of acetone
13. 13
    Sonstigedried
14. 14
    Sonstigeto afford a white solid, m.p. 207-212° C., 1.87 g (87.2%)

Vorschrift

To a 100 ml round-bottomed flask equipped with condenser and N2 inlet were added 1.43 g (4.11 mmol) 4-(4-chlorobutyl)phenyl)-2-methylthiazole hydrobromide, 0.90 g. (4.11 mmol) N-benzisothiazolylpiperazine, 0.72 g (4.11 mmol) diisopropylethyl amine, 0.87 g (8.22 mmol) sodium carbonate, 2 mg sodium iodide, and 40 ml methylisobutyl ketone. The reaction was refluxed 31 hours, cooled, filtered, and the filtrate evaporated. The residue was chromatographed on silica gel using ethyl acetate/methylene chloride as eluent to afford an oil, which was taken up in methylene chloride and precipitated by addition of ether saturated with HCl. The solid was filtered, washed with ether, dried briefly, then washed with a minimal amount of acetone and dried to afford a white solid, m.p. 207-212° C., 1.87 g (87.2%). NMR (DMSO-d6): 1.6-1.8 (m, 4H), 2.64 (t, 2H), 2.72 (s, 3H), 3.1-3.3 (m, 4H), 3.4-3.6 (m,4 H), 4.0 (d, 2H), 7.2-8.1 (m, 8H), 7.85 (s, 1H).

Quelle