Sodium Hydroxide → 1,3-Benzodioxole-5-propanamine

Participants

Reaction Steps

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).

Provenance & Evidence