Реакция #54352

Уравнение реакции

3-[4-(1,1-dimethylheptyl)-2-hydroxyphenyl]piperidine

potassium carbonate

1-bromo-2-propyne

→

3-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]-1-N-(2-propynyl)piperidine

Растворители

ethanol

Условия реакции

Обработка

1. 1
   workup.ADDITIONA mixture of 0.900 g
2. 2
   Температураat reflux for 22 hours
3. 3
   ДругоеThe reaction mixture is then evaporated
4. 4
   workup.DISSOLUTIONdissolved in 100 ml
5. 5
   ЭкстракцияThe organic extract
6. 6
   Промывкаis washed with two 150 ml
7. 7
   Сушкаportions of saturated sodium chloride, dried over magnesium sulfate
8. 8
   Другоеevaporated
9. 9
   ДругоеThe residue is purified via column chromatography on 100 g
10. 10
    Промывкаsilica gel eluted with 2% methanol-dichloromethane
11. 11
    ДругоеThe product is crystallized from pentane (117 mg., 11.5%)

Методика

A mixture of 0.900 g. (2.97 mmoles) of 3-[4-(1,1-dimethylheptyl)-2-hydroxyphenyl]piperidine, 481 mg. (3.49 mmoles) of anhydrous potassium carbonate and 353 mg. (2.97 mmoles) of 1-bromo-2-propyne in 20 ml. of ethanol is heated at reflux for 22 hours. The reaction mixture is then evaporated and dissolved in 100 ml. of saturated sodium bicarbonate and 200 ml. of dichloromethane. The organic extract is washed with two 150 ml. portions of saturated sodium chloride, dried over magnesium sulfate and evaporated. The residue is purified via column chromatography on 100 g. silica gel eluted with 2% methanol-dichloromethane. The product is crystallized from pentane (117 mg., 11.5%).

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