تفاعل #66143

معادلة التفاعل

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

المردود 80.2%

المذيبات

toluene

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture was heated
2. 2
   درجة الحرارةto reflux
3. 3
   درجة الحرارةreflux
4. 4
   workup.WAITcontinued for 28 h
5. 5
   درجة الحرارةThe reaction mixture was cooled
6. 6
   أخرىthe organic phase separated
7. 7
   استخلاصThe aqueous phase was extracted with ethyl acetate (3×5 mL)
8. 8
   غسيلwashed with water and brine
9. 9
   تجفيفdried over anhydrous sodium sulfate
10. 10
    ترشيحfiltered
11. 11
    تركيزconcentrated under vacuum
12. 12
    أخرىto give a residue which
13. 13
    أخرىwas purified by preparative TLC
14. 14
    غسيلeluting with 2% methanol in chloroform

الإجراء التجريبي

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.

المصدر