반응 #167688

반응 방정식

N,N′-dibenzylethylenediamine

diethyl bromomalonate

→

title compound

ethyl 1,4-dibenzyl-3-oxopiperazine-2-carboxylate

용매

NaOH

acetonitrile

반응 조건

후처리

1. 1
   온도(reflux) for 7 hours
2. 2
   기타The solvent was evaporated
3. 3
   기타to provide a residue that
4. 4
   추출the mixture was extracted with ethyl acetate twice
5. 5
   건조dried over Na2SO4
6. 6
   기타the solvent was evaporated
7. 7
   기타The crude mixture was purified by silica gel chromatography (Analogix IntelliFlash 280, SF40-150)
8. 8
   세척eluting with 15%-30% ethyl acetate/hexanes

실험 절차

To a solution of N,N′-dibenzylethylenediamine (14.12 mL, 60.2 mmol) in acetonitrile (100 mL) was added diethyl bromomalonate (5.14 mL, 30.1 mmol), and the mixture was heated with an oil bath at 90° C. (reflux) for 7 hours. The solvent was evaporated to provide a residue that was dissolved in 1M NaOH (aqueous), and the mixture was extracted with ethyl acetate twice, dried over Na2SO4, and the solvent was evaporated. The crude mixture was purified by silica gel chromatography (Analogix IntelliFlash 280, SF40-150) eluting with 15%-30% ethyl acetate/hexanes to afford the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 7.38-7.20 (m, 100H), 4.54 (dd, J=15.0, 154.2, 2H), 4.20-4.10 (m, 2H), 4.03 (q, J=7.1, 1H), 3.96 (s, 1H), 3.61 (dd, J=13.5, 41.7, 2H), 3.27-3.14 (m, 2H), 3.05-2.95 (m, 1H), 2.60-2.52 (m, 1H), 1.23 (t, J=7.1, 3H); MS (ESI+) m/z 353.0 (M+H)+.

출처