1-cyanomethyl-4-carboxymethyl-2-ketopiperazine, salts...

Details 1-cyanomethyl-4-carboxymethyl-2-ketopiperazine, salts... 1-cyanomethyl-4-carboxymethyl-2-ketopiperazine, salts...

C - Chemistry, Metallurgy

07

D

C07D 241/08 (2006.01) C07C 227/22 (2006.01)

Patent

CA 2085156

ABSTRACT A novel intermediate useful in the synthesis of ethylenediaminetriacetic acid (ED3A) or its salts. N,N'-ethylenediaminediacetic acid (ED2AH2) or a salt containing up to one equivalent of base cation is condensed with formaldehyde to form a stable 5-membered ring intermediate. The addition of cyanide across this cyclic material forms ethylenediamine N,N'-diacetic acid-N'-cyanomethyl or salts thereof (mononitrile-diacid), which is a useful intermediate in the production of ED3A. The nitrile in aqueous solutions may be spontaneously cyclized to form 2-oxo-1,4-piperazinediacetic acid (3KP) or salts thereof. In the presence of excess base, salts of ED3A are formed in excellent yield and purity.

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