Reacción #607461

Ecuación de reacción

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

Rendimiento 69.0%

Disolventes

isopropanol

ethanol

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONThe following were added to a 250 mL reactor
2. 2
   Otrowere 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
   Otrothe organic phase separated
5. 5
   Lavadowashed with 2 portions of 50 mL of a 5% sodium bicarbonate solution
6. 6
   Secadodry with MgSO4
7. 7
   Filtraciónfiltered
8. 8
   Otroevaporated to dryness
9. 9
   Otroyielding the raw product as a slightly yellowish oil
10. 10
    TemperaturaThis agitation was maintained for two hours in order
11. 11
    Otrothe precipitation of the hydrochloride
12. 12
    FiltraciónThe resulting solid was filtered
13. 13
    Otrovacuum dried

Procedimiento

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%).

Fuente