Реакция #312570

Уравнение реакции

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

Растворители

toluene

pyridine

Условия реакции

Обработка

1. 1
   Концентрированиеconcentrated in vacuo
2. 2
   workup.DISSOLUTIONThe residue was dissolved in CH2Cl2
3. 3
   Промывкаwashed with saturated aqueous NaHCO3 solution (100 mL)
4. 4
   ЭкстракцияThe aqueous layer was extracted with CH2Cl2 (2×50 ml)
5. 5
   Концентрированиеthe organic layer was concentrated to an oil
6. 6
   workup.DISSOLUTIONThis was dissolved in EtOAc which
7. 7
   Другоеto separate
8. 8
   ДругоеThe EtOAc layer was separated
9. 9
   Промывкаwashed with saturated aqueous NaHCO3 solution (100 mL)
10. 10
    ЭкстракцияThe aqueous layer was extracted with EtOAc (2×50 ml)
11. 11
    Промывкаthe combined organic layer was washed with saturated aqueous NaCl solution (50 ml)
12. 12
    Сушкаdried over Na2SO4
13. 13
    Фильтрацияfiltered
14. 14
    Концентрированиеconcentrated to a crude orange liquid (3.77 g, ˜100%)

Методика

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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