N-[3-{(1,4-benzodioxan-2-ylmethyl)amino}propionyl]-3,4-methylenedioxyaniline → HCID 13210215, compound

HRID 1788819Notes

Reaction equation

HRID 1788819 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[O:10][CH2:9][CH:8]1[CH2:17][NH:18][CH2:19][CH2:20][C:21]([NH:23][C:24]1[CH:29]=[CH:28][C:27]2[O:30][CH2:31][O:32][C:26]=2[CH:25]=1)=O>O1CCCC1>[O:7]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[O:10][CH2:9][CH:8]1[CH2:17][NH:18][CH2:19][CH2:20][CH2:21][NH:23][C:24]1[CH:29]=[CH:28][C:27]2[O:30][CH2:31][O:32][C:26]=2[CH:25]=1

Participants

4

Reactant 2

HCID 13210223N-[3-{(1,4-benzodioxan-2-ylmethyl)amino}propionyl]-3,4-methylenedioxyanilineHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 13210215HCID 13210215, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

In 50 ml of tetrahydrofuran is suspended 1.5 g of lithium aluminum hydride and a solution of 6.0 g of N-[3-{(1,4-benzodioxan-2-yl}methyl)amino propionyl]-3,4-methylenedioxyaniline prepared according to the procedure described in Example 6 dissolved in 10 ml of tetrahydrofuran is added dropwise to the suspension. After completion of the dropwise addition, the mixture is stirred for 4 hours at 50° C. After completion of the reaction, the reaction mixture is subjected to the post-treatment for lithium aluminum hydride in the conventional manner and the resulting precipitates including aluminum hydroxide are removed by filtration. The filtrate is concentrated and then dissolved in ethyl acetate and the resulting solution is washed with saturated sodium chloride solution and dried over anhydrous sodium sulfate. Thereafter, 20% hydrogen chloride in ethyl acetate is added and the resulting crystals are collected by filtration and recrystallized from ethanol to give 5.6 g (80%) of N-[3-{(1,4-benzodioxan-2-ylmethyl)amino}propyl]-3,4-methylenedioxyaniline.

Workup

  1. additionis added dropwise to the suspension
  2. additionAfter completion of the dropwise addition
  3. customAfter completion of the reaction
  4. customthe resulting precipitates
  5. customare removed by filtration
  6. concentrationThe filtrate is concentrated
  7. dissolutiondissolved in ethyl acetate
  8. washthe resulting solution is washed with saturated sodium chloride solution
  9. dry with materialdried over anhydrous sodium sulfate
  10. additionThereafter, 20% hydrogen chloride in ethyl acetate is added
  11. filtrationthe resulting crystals are collected by filtration
  12. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-ee7884ce19df458082f8329aee02b602
Source dataset
uspto-grants-1987_08
Patent number
US04684739

Reaction notes

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