Реакция #54347

Уравнение реакции

1-benzyl-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-(3-phenylpropyl)-4-piperidinol

thionyl chloride

→

title compound

1-benzyl-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-(3-phenylpropyl)-1,2,5,6-tetrahydropyridine

Растворители

pyridine

Условия реакции

Обработка

1. 1
   ДругоеTo a -5° C.
2. 2
   ДругоеThe reaction mixture is quenched by slow addition to 200 ml
3. 3
   ЭкстракцияThe quenched mixture is extracted with 250 ml
4. 4
   Промывкаof ether, the extract washed once with 200 ml
5. 5
   Сушка20% potassium carbonate, dried over magnesium sulfate
6. 6
   Другоеevaporated
7. 7
   ДругоеThe residue is purified via column chromatography on 300 g
8. 8
   Промывкаsilica gel eluted with 50% ether-cyclohexane

Методика

To a -5° C. solution of 3.0 g. (4.85 mmols.) of 1-benzyl-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-(3-phenylpropyl)-4-piperidinol in 5 ml. of pyridine is slowly added 2.89 g. (24.3 mmols.) of thionyl chloride. The reaction mixture is then allowed to slowly warm to 25° C. and is stirred 12 hours longers. The reaction mixture is quenched by slow addition to 200 ml. of cold 20% potassium carbonate. The quenched mixture is extracted with 250 ml. of ether, the extract washed once with 200 ml. 20% potassium carbonate, dried over magnesium sulfate and evaporated. The residue is purified via column chromatography on 300 g. silica gel eluted with 50% ether-cyclohexane to yield the title compound.

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