Triethylamine → Acetamide, N-(6-aminohexyl)-2,2,2-trifluoro-

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Reaction Steps

N-1-trifluoroacetylhexanediamine, (CF3CONH(CH2)6NH2) is prepared by adding ethyltrifluoroacetate (1.2 ml, 10 mmol) dropwise over one hour to a stirred mixture of hexanediamine (1.16 g; 10 mmol) and triethylamine (1 ml; 7 mmol) in 20 ml methanol. The solution is stirred overnight. After removal of solvents, the reaction mixture is flash chromatographed on silica using 0-25% methanol in dichloromethane. The fractions containing the desired product are pooled and concentrated to give a colorless powder (1.1 gm, yield-42.6%); melting point 52° C; 1H NMR (CDCl3, d, TMS=) .00) 7.1-7.2 (m, 3H, NH2, NH) 3.2-3.3 (m, 2H, CO--NH--CH2), 2.8-2.9 (m 2 H, CH2 --NH2) 1.2-1.6 (m, 8H,--CH--(CH2)2 --CH2 --).

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