反応 #5122

反応方程式

amide

3-(3,4-methylenedioxyphenyl)propanamide

LiAlH4

NaOH

→

3-(3,4-methylenedioxyphenyl) propylamine

収率 85.0%

溶媒

water

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   温度The reaction mixture was refluxed for 2 hours
2. 2
   ろ過The mixture was filtered through a Celite layer
3. 3
   その他to give solids, which
4. 4
   抽出This solution was extracted twice with 200 ml of ethyl ether
5. 5
   乾燥The combined organic phase was dried over magnesium sulfate
6. 6
   濃縮concentrated
7. 7
   workup.DISTILLATIONdistilled under reduced pressure

実験手順

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).

出典