반응 #71427

반응 방정식

methanesulfonic acid 5-nitro-pyridin-2-ylmethyl ester

1-(4-methoxy-benzyl)-2,2-dimethyl-piperazine

cesium carbonate

→

title compound

수율 80.2%

1-(4-Methoxy-benzyl)-2,2-dimethyl-4-(5-nitro-pyridin-2-ylmethyl)-piperazine

수율 80.2%

용매

DMF

반응 조건

후처리

1. 1
   기타quenched by addition of a saturated aqueous solution of NaHCO3
2. 2
   추출extracted with EtOAc
3. 3
   세척The organic phase was washed with a saturated aqueous solution of NaHCO3
4. 4
   건조dried (Na2SO4)
5. 5
   여과filtered
6. 6
   농축concentrated
7. 7
   기타The residue was purified by by silica gel column chromatography (DCM DCM/MeOH, 99:1)

실험 절차

A mixture of methanesulfonic acid 5-nitro-pyridin-2-ylmethyl ester (Step 112.3) (0.5 g, 2.16 mmol), 1-(4-methoxy-benzyl)-2,2-dimethyl-piperazine (Step 108.2) (0.655 g, 2.8 mmol, 1.3 equiv), cesium carbonate (0.845 g, 2.6 mmol, 1.2 equiv), and DMF (4 ml) was stirred for 5 h at rt, quenched by addition of a saturated aqueous solution of NaHCO3 and extracted with EtOAc. The organic phase was washed with a saturated aqueous solution of NaHCO3, dried (Na2SO4), filtered and concentrated. The residue was purified by by silica gel column chromatography (DCM DCM/MeOH, 99:1) to provide 0.642 g of the title compound as a red solid: ESI-MS: 371.2 [M+H]+; tR=3.18 min (System 1); TLC: Rf=0.44 (DCM/MeOH, 9:1).

출처