Preparation of N,N'-dicarboxymethyl-1,3-propanediamines

Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal

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260251R, 2604381, 260439R, 260519, C07C10102

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039883671

ABSTRACT:
N,N'-Dicarboxymethyl-1,3-propanediamine (designated PDDA) is prepared by reacting 1,3-propanediamine with formaldehyde and HCN to form hexahydropyrimidine-1,3-diacetonitrile, which is hydrolyzed with an aqueous alkali metal hydroxide to form dialkali metal hexahydropyrimidine-1,3-diacetate which, in turn, is reacted with mineral acid to form the desired PDDA and formaldehyde.
N,n'-dicarboxymethyl-2-hydroxy-1,3-propanediamine (designated HYDROXY-PDDA) is prepared by reacting 1,3-diamino-2-propanol with formaldehyde and HCN to form 5-hydroxyhexahydropyrimidine-1,3-diacetonitrile, which is hydrolyzed with an aqueous alkali metal hydroxide to form dialkali metal 5-hydroxyhexahydropyrimidine-1,3-diacetate which, in turn, is reacted with acid to form the desired HYDROXY-PDDA and formaldehyde.

REFERENCES:
patent: 2413856 (1947-01-01), Bersworth
patent: 2558923 (1951-07-01), Bersworth
patent: 3689544 (1972-09-01), Scanlon et al.
patent: 3872120 (1975-03-01), Mod et al.
Johnson et al., J. Org. Chem., vol. 27, 2077-2080, (1962).

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