Реакция #66143

Уравнение реакции

sodium hydroxide

{2-[4-(4,6-dimethyl-pyridin-2-yl)-piperazin-1-yl]-5-nitro-phenyl}-methanol

4-(3-chloro-propyl)-morpholine

→

4-(3-{2-[4-(4,6-dimethyl-pyridin-2-yl)-piperazin-1-yl]-5-nitro-benzyloxy}-propyl)-morpholine

Выход 80.2%

Растворители

toluene

Условия реакции

Обработка

1. 1
   ТемператураThe mixture was heated
2. 2
   Температураto reflux
3. 3
   Температураreflux
4. 4
   workup.WAITcontinued for 28 h
5. 5
   ТемператураThe reaction mixture was cooled
6. 6
   Другоеthe organic phase separated
7. 7
   ЭкстракцияThe aqueous phase was extracted with ethyl acetate (3×5 mL)
8. 8
   Промывкаwashed with water and brine
9. 9
   Сушкаdried over anhydrous sodium sulfate
10. 10
    Фильтрацияfiltered
11. 11
    Концентрированиеconcentrated under vacuum
12. 12
    Другоеto give a residue which
13. 13
    Другоеwas purified by preparative TLC
14. 14
    Промывкаeluting with 2% methanol in chloroform

Методика

Aqueous sodium hydroxide (50% w/w, 10 g, 125 mmol) and tetrabutylammonium hydrogen sulfate (0.20 g) were added successively to a solution of {2-[4-(4,6-dimethyl-pyridin-2-yl)-piperazin-1-yl]-5-nitro-phenyl}-methanol (0.50 g, 1.46 mmol) in toluene (5 mL). The mixture was heated to reflux with vigorous stirring for 45 min then 4-(3-chloro-propyl)-morpholine (0.50 g, 3.00 mmol) was added and reflux continued for 28 h. The reaction mixture was cooled and the organic phase separated. The aqueous phase was extracted with ethyl acetate (3×5 mL). The organic phases were combined, washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to give a residue which was purified by preparative TLC eluting with 2% methanol in chloroform to afford 4-(3-{2-[4-(4,6-dimethyl-pyridin-2-yl)-piperazin-1-yl]-5-nitro-benzyloxy}-propyl)-morpholine (550 mg, 80%) as a solid.

Источник