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

HRID 5026Notes

Reaction equation

HRID 5026 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][CH2:11][C:12]([NH2:14])=O)=[CH:4][C:3]=2[O:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>O1CCCC1.O>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][CH2:11][CH2:12][NH2:14])=[CH:4][C:3]=2[O:2]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 149144873-(1,3-Benzodioxol-5-yl)propanamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 4130151,3-Benzodioxole-5-propanamineYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

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).

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hours
  2. filtrationThe mixture was filtered through a Celite layer
  3. customto give solids, which
  4. extractionThis solution was extracted twice with 200 ml of ethyl ether
  5. dry with materialThe combined organic phase was dried over magnesium sulfate
  6. concentrationconcentrated
  7. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-34fa8b341ee347298276cad877914064
Source dataset
uspto-grants-1993_09
Patent number
US05242944

Reaction notes

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