تفاعل #607461

ord-189b2f97cecc4c6ca9715ea316809a7f

معادلة التفاعل

O=c1c2ccccc2ncn1CCCl
3-(2-chloroethyl) quinazoline-4 (3H)-one
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
[I-].[Na+]
sodium iodide
Cl
HCl
FC(F)(F)c1cccc(N2CCNCC2)c1
1-(3-(trifluoromethyl)phenyl)piperazine
Cl.O=c1c2ccccc2ncn1CCN1CCN(c2cccc(C(F)(F)F)c2)CC1
3-(2-(4-(3-(trifluoromethyl)phenyl)piperazine-1-yl)ethyl)quinazoline-4 (3H)-one hydrochloride
المردود 69.0%

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    workup.ADDITIONThe following were added to a 250 mL reactor
  2. 2
    أخرىwere 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
    أخرىthe organic phase separated
  5. 5
    غسيلwashed with 2 portions of 50 mL of a 5% sodium bicarbonate solution
  6. 6
    تجفيفdry with MgSO4
  7. 7
    ترشيحfiltered
  8. 8
    أخرىevaporated to dryness
  9. 9
    أخرىyielding the raw product as a slightly yellowish oil
  10. 10
    درجة الحرارةThis agitation was maintained for two hours in order
  11. 11
    أخرىthe precipitation of the hydrochloride
  12. 12
    ترشيحThe resulting solid was filtered
  13. 13
    أخرىvacuum dried

الإجراء التجريبي

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%).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US09326984B2uspto-grants-2016_05