反应 #54972

反应方程式

4-(4-fluorobenzoyl)piperidine

3-bromopropanol

potassium carbonate

→

product

收率 48.5%

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

收率 48.5%

溶剂

1-butanol

反应条件

后处理

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

实验过程

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.

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