反応 #607469

ord-0e42af724da44b8b86537f57c5e4cc84

反応方程式

CCc1nc2ccccc2c(=O)n1CCCl
3-(2-chloroethyl)-2-ethylquinazoline-4 (3H)-one
FC(F)(F)c1cccc(N2CCNCC2)c1
1-(3-(trifluoromethyl)phenyl)piperazine
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
[I-].[Na+]
sodium iodide
CCc1nc2ccccc2c(=O)n1CCN1CCN(c2cccc(C(F)(F)F)c2)CC1
2-ethyl-3-(2-(4-(3-(trifluoromethyl)phenyl)piperazine-1-yl)ethyl)quinazoline-4 (3H)-one
収率 98.9%

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    温度The reaction medium was heated
  2. 2
    温度to reflux
  3. 3
    その他were slowly removed with assistance from a Dean Stark
  4. 4
    その他After the end of the reaction, ethyl acetate (250 mL)
  5. 5
    温度The mixture was maintained under agitation for a period of 30 minutes
  6. 6
    その他The organic phase was separated
  7. 7
    洗浄washed with two portions of 50 mL of NaHCO3 at 5%
  8. 8
    乾燥dried with MgSO4
  9. 9
    その他evaporated at reduced pressure

実験手順

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%).

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US09326984B2uspto-grants-2016_05