تفاعل #54972

معادلة التفاعل

4-(4-fluorobenzoyl)piperidine

3-bromopropanol

potassium carbonate

→

product

المردود 48.5%

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

المردود 48.5%

المذيبات

1-butanol

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONA mixture of 60.9 g
2. 2
   درجة الحرارةat reflux for 15 hours
3. 3
   ترشيحThe mixture was filtered
4. 4
   تركيزthe filtrate concentrated under vacuum
5. 5
   workup.DISSOLUTIONthe residual oil was dissolved in acid solution
6. 6
   استخلاصextracted with benzene
7. 7
   استخلاصextracted with chloroform
8. 8
   تجفيفThe chloroform extracts were dried over anhydrous sodium sulfate
9. 9
   ترشيحthe mixture filtered
10. 10
    تركيزthe filtrate concentrated under vacuum
11. 11
    workup.ADDITIONAnhydrous ether was added to the oily residue
12. 12
    أخرىthe oil crystallized
13. 13
    غسيلwas washed with ether
14. 14
    ترشيحfiltered
15. 15
    أخرىUpon recrystallizing from isopropanol and isopropyl ether, 38.5 g

الإجراء التجريبي

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.

المصدر