Reaktion #5122

Reaktionsgleichung

amide

3-(3,4-methylenedioxyphenyl)propanamide

LiAlH4

NaOH

→

3-(3,4-methylenedioxyphenyl) propylamine

Ausbeute 85.0%

Lösungsmittel

water

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was refluxed for 2 hours
2. 2
   FiltrationThe mixture was filtered through a Celite layer
3. 3
   Sonstigeto give solids, which
4. 4
   ExtraktionThis solution was extracted twice with 200 ml of ethyl ether
5. 5
   TrocknenThe combined organic phase was dried over magnesium sulfate
6. 6
   Einengenconcentrated
7. 7
   workup.DISTILLATIONdistilled under reduced pressure

Vorschrift

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).

Quelle