反应 #312570

反应方程式

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

溶剂

toluene

pyridine

反应条件

后处理

1. 1
   浓缩concentrated in vacuo
2. 2
   workup.DISSOLUTIONThe residue was dissolved in CH2Cl2
3. 3
   洗涤washed with saturated aqueous NaHCO3 solution (100 mL)
4. 4
   萃取The aqueous layer was extracted with CH2Cl2 (2×50 ml)
5. 5
   浓缩the organic layer was concentrated to an oil
6. 6
   workup.DISSOLUTIONThis was dissolved in EtOAc which
7. 7
   其他to separate
8. 8
   其他The EtOAc layer was separated
9. 9
   洗涤washed with saturated aqueous NaHCO3 solution (100 mL)
10. 10
    萃取The aqueous layer was extracted with EtOAc (2×50 ml)
11. 11
    洗涤the combined organic layer was washed with saturated aqueous NaCl solution (50 ml)
12. 12
    干燥dried over Na2SO4
13. 13
    过滤filtered
14. 14
    浓缩concentrated to a crude orange liquid (3.77 g, ˜100%)

实验过程

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);

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