تفاعل #54352

معادلة التفاعل

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

المذيبات

ethanol

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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%).

المصدر