Reaktion #55340

Reaktionsgleichung

NaOH

3-dimethylaminopropyl chloride

2-hydroxy-3',4'-dichlorobibenzyl

sodium hydride

→

2-(3-dimethylaminopropoxy)-3',4'-dichlorobibenzyl hydrochloride

Ausbeute 142.9%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturunder cooling
2. 2
   workup.STIRRINGstirred for 5 hours
3. 3
   workup.ADDITIONwas added
4. 4
   Extraktionthe product was extracted with ether
5. 5
   ExtraktionThe ether extract
6. 6
   Waschenwas washed well with saturated sodium chloride solution
7. 7
   Trocknendried over anhydrous sodium sulfate
8. 8
   workup.DISTILLATIONdistilled in vacuo to sufficiently remove ether
9. 9
   workup.DISSOLUTIONThe resultant residue was dissolved in ether
10. 10
    workup.ADDITION20% ethanolic hydrogen chloride was added
11. 11
    Sonstigeto yield a precipitate
12. 12
    SonstigeRecrystallization from ethanol-ether

Vorschrift

To a solution of 2.5 g of 2-hydroxy-3',4'-dichlorobibenzyl in 10 ml of dimethylformamide was added 0.23 g of sodium hydride under cooling. The mixture was stirred for 30 minutes and to this was added dropwise 2.2 g of 3-dimethylaminopropyl chloride. The reaction mixture was warmed to about 60° C. and then stirred for 5 hours. Upon completion of the reaction, 2N-NaOH aqueous solution was added, and the product was extracted with ether. The ether extract was washed well with saturated sodium chloride solution, dried over anhydrous sodium sulfate and then distilled in vacuo to sufficiently remove ether and a small amount of the remaining 3-dimethylaminopropyl chloride. The resultant residue was dissolved in ether and then 20% ethanolic hydrogen chloride was added to yield a precipitate. Recrystallization from ethanol-ether gave 2.6 g (71% yield) of 2-(3-dimethylaminopropoxy)-3',4'-dichlorobibenzyl hydrochloride, m. p. 136°-137° C.

Quelle