반응 #312570

반응 방정식

3-(2-Benzyl-2-aza-bicyclo[3.3.1]non-5-yl)-phenylamine

2-methoxy-ethanesulfonyl chloride

→

2-Methoxy-ethanesulfonic acid [3-(2-benzyl-2-aza-bicyclo[3.3.1]non-5-yl)-phenyl]-amide

용매

toluene

pyridine

반응 조건

후처리

1. 1
   농축concentrated in vacuo
2. 2
   workup.DISSOLUTIONThe residue was dissolved in CH2Cl2
3. 3
   세척washed with saturated aqueous NaHCO3 solution (100 mL)
4. 4
   추출The aqueous layer was extracted with CH2Cl2 (2×50 ml)
5. 5
   농축the organic layer was concentrated to an oil
6. 6
   workup.DISSOLUTIONThis was dissolved in EtOAc which
7. 7
   기타to separate
8. 8
   기타The EtOAc layer was separated
9. 9
   세척washed with saturated aqueous NaHCO3 solution (100 mL)
10. 10
    추출The aqueous layer was extracted with EtOAc (2×50 ml)
11. 11
    세척the combined organic layer was washed with saturated aqueous NaCl solution (50 ml)
12. 12
    건조dried over Na2SO4
13. 13
    여과filtered
14. 14
    농축concentrated to a crude orange liquid (3.77 g, ˜100%)

실험 절차

3-(2-Benzyl-2-aza-bicyclo[3.3.1]non-5-yl)-phenylamine (2.71 g, 8.84 mmol) stirred in pyridine (25 ml) at 0° C. was charged with 2-methoxy-ethanesulfonyl chloride (2.1 g, 13.26 mmol) dropwise causing a color change from yellow to bright orange. The reaction was allowed to warm to room temperature gradually and stirred 18 h. The reaction mixture was diluted with toluene and concentrated in vacuo. The residue was dissolved in CH2Cl2 and washed with saturated aqueous NaHCO3 solution (100 mL). The aqueous layer was extracted with CH2Cl2 (2×50 ml) and the organic layer was concentrated to an oil. This was dissolved in EtOAc which caused an oil to separate. The EtOAc layer was separated and washed with saturated aqueous NaHCO3 solution (100 mL). The aqueous layer was extracted with EtOAc (2×50 ml) and the combined organic layer was washed with saturated aqueous NaCl solution (50 ml), dried over Na2SO4, filtered and concentrated to a crude orange liquid (3.77 g, ˜100%). (TLC 75% EtOAc/hexanes Rf 0.48);

출처