反応 #54972

反応方程式

4-(4-fluorobenzoyl)piperidine

3-bromopropanol

potassium carbonate

→

product

収率 48.5%

4-(4-Fluorobenzoyl)-1-(3-hydroxypropyl)piperidine

収率 48.5%

溶媒

1-butanol

反応条件

後処理

1. 1
   workup.ADDITIONA mixture of 60.9 g
2. 2
   温度at reflux for 15 hours
3. 3
   ろ過The mixture was filtered
4. 4
   濃縮the filtrate concentrated under vacuum
5. 5
   workup.DISSOLUTIONthe residual oil was dissolved in acid solution
6. 6
   抽出extracted with benzene
7. 7
   抽出extracted with chloroform
8. 8
   乾燥The chloroform extracts were dried over anhydrous sodium sulfate
9. 9
   ろ過the mixture filtered
10. 10
    濃縮the filtrate concentrated under vacuum
11. 11
    workup.ADDITIONAnhydrous ether was added to the oily residue
12. 12
    その他the oil crystallized
13. 13
    洗浄was washed with ether
14. 14
    ろ過filtered
15. 15
    その他Upon recrystallizing from isopropanol and isopropyl ether, 38.5 g

実験手順

A mixture of 60.9 g. (0.293 mole) of 4-(4-fluorobenzoyl)piperidine, 46.0 g. (0.31 mole) of 3-bromopropanol and 41.4 g. (0.30 mole) of anhydrous potassium carbonate in 750 ml. of 1-butanol was stirred at reflux for 15 hours. The mixture was filtered, the filtrate concentrated under vacuum and the residual oil was dissolved in acid solution and extracted with benzene. After discarding the benzene layer, the aqueous acid layer was made basic and extracted with chloroform. The chloroform extracts were dried over anhydrous sodium sulfate, the mixture filtered and the filtrate concentrated under vacuum. Anhydrous ether was added to the oily residue and the oil crystallized. The solid which weighed 57.0 g. was washed with ether and filtered. Upon recrystallizing from isopropanol and isopropyl ether, 38.5 g. (48.5%) of product was obtained. A portion (4.0 g.) was recrystallized from petroleum ether to give 2.4 g. of product melting at 105°-110° C.

出典