반응 #55335

반응 방정식

water

2-chloro-N,N-dimethylethylamine

lithium hydride

2-hydroxybibenzyl

→

2-(2-dimethylaminoethoxy)bibenzyl hydrochloride

수율 95.1%

용매

toluene

toluene

toluene

반응 조건

후처리

1. 1
   온도The mixture was heated
2. 2
   온도under reflux for 30 minutes
3. 3
   온도under reflux over 5 minutes
4. 4
   온도reflux
5. 5
   기타The toluene layer was separated
6. 6
   세척washed twice with water
7. 7
   건조dried over anhydrous sodium sulfate
8. 8
   workup.DISTILLATIONthe toluene distilled off in vacuo
9. 9
   workup.DISSOLUTIONThe residue was dissolved in ethyl ether
10. 10
    workup.ADDITION20% ethanolic hydrogen chloride solution was added
11. 11
    여과The resulting precipitate was collected by filtration
12. 12
    기타recrystallized from ethanol-ether

실험 절차

To a suspension of 1.0 g of lithium hydride in 30 ml of toluene was added dropwise a solution of 3.96 g of 2-hydroxybibenzyl in 30 ml of toluene at room temperature over 5 minutes. The mixture was heated under reflux for 30 minutes, a solution of 6.45 g of 2-chloro-N,N-dimethylethylamine in 20 ml of toluene added dropwise under reflux over 5 minutes and then reflux was continued for an additional 2 hours. The reaction mixture was cooled to room temperature, and to this was added 50 ml of water. The toluene layer was separated, washed twice with water, dried over anhydrous sodium sulfate and then the toluene distilled off in vacuo. The residue was dissolved in ethyl ether, and then 20% ethanolic hydrogen chloride solution was added. The resulting precipitate was collected by filtration and recrystallized from ethanol-ether to give 5.81 g (95% yield) of 2-(2-dimethylaminoethoxy)bibenzyl hydrochloride, m. p. 172°-173° C.

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