反応 #1907191

反応方程式

Hydrochloric acid

4-(4-Chlorophenyl)piperidine hydrochloride

potassium carbonate

3-butyn-1-ol

triethylamine

methanesulfonyl chloride

→

title compound

収率 52.9%

1-(3-butynyl)-4-(4-chlorophenyl)piperidine

収率 52.9%

溶媒

acetonitrile

tetrahydrofuran

Ethyl acetate

反応条件

後処理

1. 1
   洗浄the mixrture was washed with saturated brine
2. 2
   乾燥dried over anhydrous sodium sulfate
3. 3
   その他The solvent was evaporated under reduced pressure
4. 4
   workup.STIRRINGthe mixture was stirred at 60° C. for 16 hrs
5. 5
   洗浄the mixture was washed with ethyl acetate
6. 6
   抽出the mixture was extracted with ethyl acetate
7. 7
   洗浄The extract was washed with saturated brine
8. 8
   乾燥dried over anhydrous sodium sulfate
9. 9
   その他The solvent was evaporated under reduced pressure

実験手順

To a solution (50 ml) of 3-butyn-1-ol (700 mg, 10.0 mmol) and triethylamine (2.05 ml, 15 mmol) in tetrahydrofuran was added methanesulfonyl chloride (1.72 g, 15 mmol) at 0° C., and the mixture was stirred at room temperature for 1 hr. Ethyl acetate was added to the reaction mixture, and the mixrture was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. 4-(4-Chlorophenyl)piperidine hydrochloride (2.30 g, 10.0 mmol), potassium carbonate (1.38 g, 10.0 mmol) and acetonitrile (50 ml) were added to the obtained residue, and the mixture was stirred at 60° C. for 16 hrs. 2N Hydrochloric acid was added to the reaction mixture, and the mixture was washed with ethyl acetate. The aqueous layer was basified with 8N aqueous sodium hydroxide solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (1.31 g) as a solid.

出典