Reaktion #607461

Reaktionsgleichung

3-(2-chloroethyl) quinazoline-4 (3H)-one

sodium carbonate

sodium iodide

HCl

1-(3-(trifluoromethyl)phenyl)piperazine

→

3-(2-(4-(3-(trifluoromethyl)phenyl)piperazine-1-yl)ethyl)quinazoline-4 (3H)-one hydrochloride

Ausbeute 69.0%

Lösungsmittel

isopropanol

ethanol

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONThe following were added to a 250 mL reactor
2. 2
   Sonstigewere removed slowly with the assistance of a Dean-Stark
3. 3
   workup.ADDITIONTo the resulting mixture, 100 mL of an aqueous solution of acetic acid were added at 10% and 150 mL of ethyl acetate
4. 4
   Sonstigethe organic phase separated
5. 5
   Waschenwashed with 2 portions of 50 mL of a 5% sodium bicarbonate solution
6. 6
   Trocknendry with MgSO4
7. 7
   Filtrationfiltered
8. 8
   Sonstigeevaporated to dryness
9. 9
   Sonstigeyielding the raw product as a slightly yellowish oil
10. 10
    TemperaturThis agitation was maintained for two hours in order
11. 11
    Sonstigethe precipitation of the hydrochloride
12. 12
    FiltrationThe resulting solid was filtered
13. 13
    Sonstigevacuum dried

Vorschrift

The following were added to a 250 mL reactor: 3-(2-chloroethyl) quinazoline-4 (3H)-one (1 g, 4.79 mmol), 1-(3-(trifluoromethyl)phenyl)piperazine (1,103 g, 4.79 mmol), sodium carbonate (0.762 g, 7.19 mmol), sodium iodide (0.072 g, 0.479 mmol), ethanol (50 ml) and toluene (150 ml). The reaction medium was kept under agitation and reflux for a period of twenty hours, during which 150 ml of the solvent were removed slowly with the assistance of a Dean-Stark. To the resulting mixture, 100 mL of an aqueous solution of acetic acid were added at 10% and 150 mL of ethyl acetate. The mixture was agitated, the organic phase separated, washed with 2 portions of 50 mL of a 5% sodium bicarbonate solution, dry with MgSO4, filtered and evaporated to dryness, yielding the raw product as a slightly yellowish oil. This oil was dissolved in isopropanol, adding 2 mL of concentrated HCl under agitation to the resulting solution. This agitation was maintained for two hours in order to complete the precipitation of the hydrochloride. The resulting solid was filtered and vacuum dried, yielding 1.45 g of 3-(2-(4-(3-(trifluoromethyl)phenyl)piperazine-1-yl)ethyl)quinazoline-4 (3H)-one hydrochloride (3.3 mmol, yield=69%).

Quelle