Cation-exchange chromatography and selective complexation in the isolation of branched acyclic polyamines : Syntheses of Ethylidynetris(methanamine) [tame], 2,2-Bis(aminomethyl)propan-1-ol [hmmp], 4,4',4''-Ethylidynetris(3-azabutan-1-amine) [sen] and 5,5',5'-Ethylidynetris(4-azapentan-1-amine) [stn]

Abstract

Large-scale syntheses of ethylidynetris(methanamine)* (tame), 2,2-bis(aminomethyl)propan-1-ol* (hmmp), 4,4',4?-ethylidynetris(3-azabutan-1-amine)* (sen) and 5,5',5''-ethylidynetris(4-azapentan-1-amine)* (stn) are described. The pure hydrochloride salts of tame, hmmp, sen and stn are isolated directly from the crude amine mixtures by acidification and cation-exchange chromatography. Alternatively, selective complexation as [Co(hexamine)] Cl3 followed by Zn/HCl reduction and cation-exchange chromatography is used to isolate the hexamines sen and stn as their hexahydrochloride salts. These isolation procedures are exceptionally efficient compared with the conventional solvent extraction and (often pyrolytic) high-vacuum distillation methods.

1,1,1-Tris(phenylsulfonyloxymethyl)ethane

“…We report here the title compound, (I) which is the precursor compound for branched acyclic polyamine ligands of the metal cage complexes (Geue & Searle, 1983). The structure of (I), with the atom-numbering scheme, is shown in Fig.…”

Synthesis and electrochemistry of [Pt(tame)2]4+: crystallographic analysis of bis[1,1,1-tris(aminomethyl)ethane-N,N ′]platinum(II) bis(tetrachlorozincate) dihydrate

“…The compound tameؒ3HCl (25.5 g) prepared as described previously 19 was suspended in hot ethanol (1 L) and added slowly to a warm solution of NaOH (13.5 g) in ethanol (200 mL). The mixture was heated at reflux under a stream of nitrogen for 3 h. The ethanol was evaporated and the tame ligand extracted from the white residue using hot chloroform.…”

TAME‐Hex A − A Novel Bifunctional Chelating Agent for Radioimmunoimaging

“…1,1,1‐Tris(aminomethyl)ethane (TAME) (Figure 1) is a tridentate ligand which is used as a starting material in the synthesis of more complex ligands 6,7. Salicylaldimines of TAME are used as chelating agents in the complete encapsulation of Ga 3+ ions 8.…”