반응 #58497

반응 방정식

1-chloroethyl chloroformate

2,4,6-trifluoro-N-[6-(1-methyl-piperidin-4-ylcarbonyl)-pyridin-2-yl]-benzamide

1-chloroethyl chloroformate

→

title compound

수율 29.3%

2,4,6-Trifluoro-N-[6-(piperidin-4-ylcarbonyl)-pyridin-2-yl]-benzamide

수율 29.3%

용매

dichloroethane

반응 조건

후처리

1. 1
   온도heat
2. 2
   온도at reflux for 1 hr
3. 3
   온도heat
4. 4
   온도at reflux overnight
5. 5
   농축Add methanol (10 mL) to the reaction mixture, concentrate to a small volume
6. 6
   workup.ADDITIONdilute with methanol again
7. 7
   세척load onto an SCX column (10 g), wash with methanol
8. 8
   세척elute with 2M NH3-methanol
9. 9
   기타evaporate
10. 10
    기타purify on a silica gel column (CH2Cl2 with 2 M NH3 in methanol)

실험 절차

Add 1-chloroethyl chloroformate (0.8 g) into a solution of 2,4,6-trifluoro-N-[6-(1-methyl-piperidin-4-ylcarbonyl)-pyridin-2-yl]-benzamide (0.216 g) in dichloroethane (10 mL) and heat at reflux for 1 hr. Then add more 1-chloroethyl chloroformate (1 mL) and heat at reflux overnight. Add methanol (10 mL) to the reaction mixture, concentrate to a small volume, dilute with methanol again, load onto an SCX column (10 g), wash with methanol, and elute with 2M NH3-methanol, evaporate and purify on a silica gel column (CH2Cl2 with 2 M NH3 in methanol) to obtain the title compound (61 mg). Mass spectrum (electric spray) m/z=364 (M+1); 1H NMR (CDCl3): 8.55 (d, J=8.1 Hz, 1H), 7.92 (dd, J=8.0, 8.0 Hz 1H), 7.84(1H, J=8.0 Hz, 1H), 6.81 (m, 3H), 3.89 (m, 1H), 3.12 (br d, 2H), 2.81 (m, 2H), 1.85 (m, 2H), 1.74 (br, 2H), 1.61 (m, 2H).

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