반응 #5122

반응 방정식

amide

3-(3,4-methylenedioxyphenyl)propanamide

LiAlH4

NaOH

→

3-(3,4-methylenedioxyphenyl) propylamine

수율 85.0%

용매

water

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   온도The reaction mixture was refluxed for 2 hours
2. 2
   여과The mixture was filtered through a Celite layer
3. 3
   기타to give solids, which
4. 4
   추출This solution was extracted twice with 200 ml of ethyl ether
5. 5
   건조The combined organic phase was dried over magnesium sulfate
6. 6
   농축concentrated
7. 7
   workup.DISTILLATIONdistilled under reduced pressure

실험 절차

6.0 g of the above amide was dissolved in 100 ml of dry tetrahydrofuran, which was added dropwise to a suspension of 2.4 g of LiAlH4 in 150 ml of dry tetrahydrofuran. The reaction mixture was refluxed for 2 hours and 10 ml of 1N NaOH was added thereto. The mixture was filtered through a Celite layer to give solids, which were dissolved in 200 ml of distilled water. This solution was extracted twice with 200 ml of ethyl ether. The combined organic phase was dried over magnesium sulfate, concentrated and distilled under reduced pressure to provide 4.71 g(yield 85%) of 3-(3,4-methylenedioxyphenyl) propylamine, having the characteristics of: NMR(CDCl3, 200 MHz) δ1.34 (br s, 2H, NH2), 1.72(m, J=7 Hz, 2H, CH2), 2.57(t, J=7 Hz, 2H, CH2), 2.71(t, J=7 Hz, 2H, CH2N), 5.91(s, 2H, CH2O2), 6.59-6.74(s, 3H, ArH).

출처