반응 #54972

반응 방정식

4-(4-fluorobenzoyl)piperidine

3-bromopropanol

potassium carbonate

→

product

수율 48.5%

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

수율 48.5%

용매

1-butanol

반응 조건

후처리

1. 1
   workup.ADDITIONA mixture of 60.9 g
2. 2
   온도at reflux for 15 hours
3. 3
   여과The mixture was filtered
4. 4
   농축the filtrate concentrated under vacuum
5. 5
   workup.DISSOLUTIONthe residual oil was dissolved in acid solution
6. 6
   추출extracted with benzene
7. 7
   추출extracted with chloroform
8. 8
   건조The chloroform extracts were dried over anhydrous sodium sulfate
9. 9
   여과the mixture filtered
10. 10
    농축the filtrate concentrated under vacuum
11. 11
    workup.ADDITIONAnhydrous ether was added to the oily residue
12. 12
    기타the oil crystallized
13. 13
    세척was washed with ether
14. 14
    여과filtered
15. 15
    기타Upon recrystallizing from isopropanol and isopropyl ether, 38.5 g

실험 절차

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.

출처