Ethylenediamine Dihydrochloride → Ethylenediamine

HRID 1928

Reaction equation

HRID 1928 reaction equation
[CH2:1]1[CH:6]([CH2:7][N:8]2[C:13](=[O:14])[CH:12]=[CH:11][C:9]2=[O:10])[CH2:5][CH2:4][CH:3]([C:15]([O:17][N:18]2[C:23](=[O:24])[CH:22]([S:25]([O-:28])(=[O:27])=[O:26])[CH2:21][C:19]2=[O:20])=[O:16])[CH2:2]1.[Na+:29].Cl.Cl.[CH2:32]([NH2:35])[CH2:33][NH2:34].C1C=CC(C2C(=O)C3(OC(=O)C4C3=CC=CC=4)OC=2)=CC=1>C([O-])(=O)C.[Na+]>[CH2:32]([NH2:35])[CH2:33][NH2:34].[CH2:1]1[CH:6]([CH2:7][N:8]2[C:9](=[O:10])[CH:11]=[CH:12][C:13]2=[O:14])[CH2:5][CH2:4][CH:3]([C:15]([O:17][N:18]2[C:23](=[O:24])[CH:22]([S:25]([O-:28])(=[O:27])=[O:26])[CH2:21][C:19]2=[O:20])=[O:16])[CH2:2]1.[Na+:29]

Participants

6

Reactant 3

HCID 9521Ethylenediamine DihydrochlorideHCID 37927FluorescamineHCID 4618794Sulfo-SMCC sodium

Product 2

HCID 3301EthylenediamineHCID 4618794Sulfo-SMCC sodium

Reagents, catalysts & solvents 1

HCID 517045Sodium AcetateSolvent

Procedure

Sulfo-SMCC (1 eq.)(Pierce Chemical Co., Rockford, Ill.) is dissolved in sodium acetate buffer (pH 7) and ethylenediamine dihydrochloride (5 eq.) is added. The reaction is monitored by TLC visualized with fluorescamine. When reaction is complete the reaction mixture is applied directly to a C18 reverse-phase HPLC column and eluted with a gradient of acetonitrile in triethanolamine/water, pH 7. The excess ethylene diamine elutes at the solvent front, followed by the desired product. A small amount of double coupled material formed by the condensation of one molecule of ethylenediamine with two molecules of sulfo-SMCC elutes last. The desired material is characterized by 1H NMR and IR spectroscopy, mass spectrometry, and elemental analysis.

Workup

  1. customWhen reaction
  2. washeluted with a gradient of acetonitrile in triethanolamine/water, pH 7

Sources & evidence

ORD record
ord-c0cd0c63904c42eabebf3989bb71e6b3
Source dataset
uspto-grants-1998_03
Patent number
US05728369

Linked notes

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