Reaction #607469
ord-0e42af724da44b8b86537f57c5e4cc84
Reaction equation
Reactants
Reagents
Solvents
Conditions
Workup
- 1TemperatureThe reaction medium was heated
- 2Temperatureto reflux
- 3Otherwere slowly removed with assistance from a Dean Stark
- 4OtherAfter the end of the reaction, ethyl acetate (250 mL)
- 5TemperatureThe mixture was maintained under agitation for a period of 30 minutes
- 6OtherThe organic phase was separated
- 7Washwashed with two portions of 50 mL of NaHCO3 at 5%
- 8Dryingdried with MgSO4
- 9Otherevaporated at reduced pressure
Procedure
3-(2-chloroethyl)-2-ethylquinazoline-4 (3H)-one (1.5 g; 6.34 mmol), 1-(3-(trifluoromethyl)phenyl)piperazine (1.459 g; 6.34 mmol), sodium carbonate (0.672 g; 6.34 mmol), sodium iodide (0.95 g; 6.34 mmol), ethanol (100 mL) and toluene (200 mL) were added to a 100 mL reactor. The reaction medium was heated to reflux and kept under agitation for a period of 24 hours, during which 250 mL of solvent were slowly removed with assistance from a Dean Stark. The reaction was monitored through CG/MS until completion. After the end of the reaction, ethyl acetate (250 mL) was added, together with an aqueous solution of acetic acid (100 mL; 10%). The mixture was maintained under agitation for a period of 30 minutes. The organic phase was separated, washed with two portions of 50 mL of NaHCO3 at 5%, dried with MgSO4 and evaporated at reduced pressure, yielding a pale yellow colored oil (2.7 g of raw 2-ethyl-3-(2-(4-(3-(trifluoromethyl)phenyl)piperazine-1-yl)ethyl)quinazoline-4 (3H)-one). This oil was dissolved in isopropanol, adding 2.0 mL of concentrated HCl to the resulting solution. The solution was kept under agitation at room temperature, until completing precipitation of the solids. The solids were vacuum filtered, washed with two portions of 5 mL of isopropanol and dried, yielding 2-ethyl-3-(2-(4-(3-(trifluoromethyl)phenyl)piperazine-1-yl)ethyl)quinazoline-4 (3H)-one hydrochloride as a pale white solid (2.36 g, 5.48 mmol, yield: 87%).