반응 #648249

반응 방정식

E-4-fluorocinnamic acid

TBTU

1-isopropylpiperazine

→

10A

수율 80.0%

(E)-3-(4-Fluorophenyl)-1-(4-isopropylpiperazin-1-yl)prop-2-en-1-one

수율 80.0%

용매

DMF

반응 조건

후처리

1. 1
   농축before being concentrated under reduced pressure, wherein the crude residue
2. 2
   workup.DISSOLUTIONwas dissolved in EtOAc (70 mL)
3. 3
   기타partitioned with sat. aq. NaHCO3 (25 mL)
4. 4
   기타The aq. layer was separated
5. 5
   추출further extracted with EtOAc (2×30 mL)
6. 6
   세척The combined organic layers were then washed with sat. aq. NaHCO3 (2×20 mL) and brine (35 mL)
7. 7
   농축concentrated in vacuo
8. 8
   세척gradient elution
9. 9
   workup.WAIT100% DCM for 5 min
10. 10
    workup.WAIT0% to 2% MeOH/DCM over 5 min
11. 11
    workup.WAIThold for 5 min
12. 12
    workup.WAIT2% to 4% over 5 min
13. 13
    workup.WAIThold for 5 min
14. 14
    workup.WAIT4% to 10% over 5 min
15. 15
    기타for 5 min

실험 절차

To a solution of E-4-fluorocinnamic acid (1.18 g, 7. 10 mmol), which is commercially available from Sigma-Aldrich, and TBTU (3.42 g, 10.6 mmol) in DMF (50 mL) was added 1-isopropylpiperazine (1.12 mL, 7.81 mmol) at ambient temperature. The reaction was stirred for ca. 15.5 h before being concentrated under reduced pressure, wherein the crude residue was dissolved in EtOAc (70 mL) and partitioned with sat. aq. NaHCO3 (25 mL). The aq. layer was separated and further extracted with EtOAc (2×30 mL). The combined organic layers were then washed with sat. aq. NaHCO3 (2×20 mL) and brine (35 mL), then concentrated in vacuo. The resulting residue was subjected to flash chromatography (SiO2—40 g; gradient elution: 100% DCM for 5 min, then 0% to 2% MeOH/DCM over 5 min; hold for 5 min, 2% to 4% over 5 min, hold for 5 min, 4% to 10% over 5 min, hold 10% MeOH/DCM for 5 min at 40 mL/min) to give 1.58 g 10A (80% yield) as a pale orange solid. m/z (ES+) M+1=277.4; HPLC tR=1.50 min. 1H NMR (500 MHz, CDCl3) δ 7.62 (d, J=15.6 Hz, 1H), 7.50 (dd, J=8.9, 5.5 Hz, 2H), 7.11-6.99 (m, 2H), 6.80 (d, J=15.6 Hz, 1H), 3.85-3.54 (m, 4H), 2.73 (quintet, J=6.7 Hz, 1H), 2.55 (d, J=5.2 Hz, 4H), 1.05 (d, J=6.4 Hz, 6H).

출처