반응 #54352

반응 방정식

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

용매

ethanol

반응 조건

후처리

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

실험 절차

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%).

출처