تفاعل #78236

معادلة التفاعل

4′-methoxy-N-methylacetanilide

lithium diisopropylamide

1-benzylpiperidin-4-one

diisopropylamine

n-butyl lithium

→

titled compound

المردود 69.7%

N-(4-methoxyphenyl)-N-methyl-2-(1-benzyl-4-hydroxypiperidin-4-yl)acetamide

المردود 69.7%

المذيبات

water

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe resulting mixture was stirred at −78° C. for 10 minutes
2. 2
   درجة الحرارةAfter increasing the temperature to room temperature
3. 3
   استخلاصthe mixed solution was extracted with ethyl acetate
4. 4
   غسيلThe organic layer was washed with water and saturated brine
5. 5
   تجفيفdried over anhydrous sodium sulfate
6. 6
   workup.DISTILLATIONby distilling off the solvent under reduced pressure
7. 7
   أخرىThe residue obtained
8. 8
   أخرىwas recrystallized from ether-hexane

الإجراء التجريبي

A solution of 4′-methoxy-N-methylacetanilide (12 g) in an anhydrous tetrahydrofuran (30 mL) was added to a solution in an anhydrous tetrahydrofuran (100 mL) of lithium diisopropylamide prepared from diisopropylamine (10.5 mL) and n-butyl lithium (1.53M hexane solution; 48 mL) at below −65° C., and the mixture was stirred at −78° C. for 15 minutes. An anhydrous tetrahydrofuran solution (20 mL) of 1-benzylpiperidin-4-one (12.7 g) was then added to this reaction mixture at below −65° C., and the resulting mixture was stirred at −78° C. for 10 minutes. After increasing the temperature to room temperature, water was added to the mixture, and the mixed solution was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried over anhydrous sodium sulfate, followed by distilling off the solvent under reduced pressure. The residue obtained was recrystallized from ether-hexane to obtain the titled compound (17.2 g).

المصدر