反応 #54352

反応方程式

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

溶媒

ethanol

反応条件

後処理

1. 1
   workup.ADDITIONA mixture of 0.900 g
2. 2
   温度at reflux for 22 hours
3. 3
   その他The reaction mixture is then evaporated
4. 4
   workup.DISSOLUTIONdissolved in 100 ml
5. 5
   抽出The organic extract
6. 6
   洗浄is washed with two 150 ml
7. 7
   乾燥portions of saturated sodium chloride, dried over magnesium sulfate
8. 8
   その他evaporated
9. 9
   その他The residue is purified via column chromatography on 100 g
10. 10
    洗浄silica gel eluted with 2% methanol-dichloromethane
11. 11
    その他The product is crystallized from pentane (117 mg., 11.5%)

実験手順

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%).

出典