Ethylenediamine → N-(2-Aminoethyl)-1,3-benzodioxole-5-carboxamide

HRID 2255110Notes

Reaction equation

HRID 2255110 reaction equation
[CH2:1]1[O:13][C:12]2[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=O)=[CH:4][C:3]=2[O:2]1.[CH2:14]([NH2:17])[CH2:15][NH2:16]>>[NH2:16][CH2:15][CH2:14][NH:17][C:6]([C:5]1[CH:10]=[CH:11][C:12]2[O:13][CH2:1][O:2][C:3]=2[CH:4]=1)=[O:8]

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 67590Methyl piperonylate

Product 1

HCID 13536947N-(2-Aminoethyl)-1,3-benzodioxole-5-carboxamideYield 41.9%

Procedure

7 g (0.039 mol) of methyl 3,4-methylenedioxybenzoate and 8.5 ml (0.126 mol) of ethylenediamine are heated to 100° (bath temperature) for 2.5 hours. After cooling, the excess ethylenediamine is removed in a high vacuum. The residue is acidified with dilute hydrochloric acid and extracted with chloroform. The aqueous phase is made alkaline with sodium hydroxide solution and then extracted several times with chloroform. After evaporating the solvent and recrystallizing the residue from chloroform/hexane, there are obtained 3.4 g of N-(2-aminoethyl)-1,3-benzdioxol-5-carboxamide, m.p. 120°-123°. The hydrochloride melts at 210°-213°.

Workup

  1. temperatureAfter cooling
  2. customthe excess ethylenediamine is removed in a high vacuum
  3. extractionextracted with chloroform
  4. extractionextracted several times with chloroform
  5. customAfter evaporating the solvent
  6. customrecrystallizing the residue from chloroform/hexane, there

Sources & evidence

ORD record
ord-538bdc0098a6475585cbe34c26b942c0
Source dataset
uspto-grants-1993_08
Patent number
US05238962

Reaction notes

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