Reaktion #54972

Reaktionsgleichung

4-(4-fluorobenzoyl)piperidine

3-bromopropanol

potassium carbonate

→

product

Ausbeute 48.5%

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

Ausbeute 48.5%

Lösungsmittel

1-butanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONA mixture of 60.9 g
2. 2
   Temperaturat reflux for 15 hours
3. 3
   FiltrationThe mixture was filtered
4. 4
   Einengenthe filtrate concentrated under vacuum
5. 5
   workup.DISSOLUTIONthe residual oil was dissolved in acid solution
6. 6
   Extraktionextracted with benzene
7. 7
   Extraktionextracted with chloroform
8. 8
   TrocknenThe chloroform extracts were dried over anhydrous sodium sulfate
9. 9
   Filtrationthe mixture filtered
10. 10
    Einengenthe filtrate concentrated under vacuum
11. 11
    workup.ADDITIONAnhydrous ether was added to the oily residue
12. 12
    Sonstigethe oil crystallized
13. 13
    Waschenwas washed with ether
14. 14
    Filtrationfiltered
15. 15
    SonstigeUpon recrystallizing from isopropanol and isopropyl ether, 38.5 g

Vorschrift

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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