Ethyl chloroformate → Tris(2-carbethoxyaminoethyl)amine

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In accord with the procedure of H. Schmidt et al., Z. anoro. allq. Chem., 578, 75 (1989), ethylchloroformate (33.4 g, 0.310 mol) was added dropwise to a solution of tris(2-aminoethyl)amine (TREN) (29.2 g, 0.20 mol) dissolved in a mixture of benzene (225 mL) and water (100 mL) cooled to 5° C. After the addition was completed, KOH (36.4 g, 0.650 mol) dissolved in water (35 mL) was added dropwise simultaneously with more ethylchloroformate (33.4 g, 0.310 mol). The reaction mixture was stirred for 2 hr. at 5° C. and then for 8 hr. at room temperature. The benzene layer was separated and the water layer extracted with chloroform (2×100 mL). The combined organic fractions were dried over MgSO4, decanted and the decantate evaporated to dryness to give the intermediate tris(2-carbethoxyaminoethyl)amine (5) in 85% yield as a thick oil which was used in subsequent reactions without further purification (1H NMR (CDCl3)δ1.27 (9H, t, 3JHH =7.1 Hz), δ2.60 (6H, t, 3JHH =5.7 Hz), δ3.23 (6H, br), δ4.10 (6H, q, 3J=7.1 5.50 (3H, br); IR 3300, 1720, 1530, 1250 cm-1).

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