Triethylamine → N-heptyl-N-ethyladipamic acid, methyl ester

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Reaction Steps

To a solution of 3.2 gms of the N-heptyl-N-ethylamine in 96 ml of CH2Cl2 are added 5.7 ml of Et3N followed by 3.63 ml of hexanedioic acid monochloride monomethyl ester. This mixture is stirred at room temperature for 18 hours; and after concentrating under vacuum, the residue obtained is partitioned between ethyl acetate and an aqueous 2N HCl solution. The organic layer is separated and washed with aqueous saturated NaHCO3, then brine, and dried over MgSO4. Following filtration and concentration under vacuum, the residue is flash chromatographed on normal phase silica gel using a 3/1 ratio of hexane and ethyl acetate to yield N-heptyl-N-ethyladipamic acid, methyl ester.

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