Water → N1-[2-(2-aminoethoxy)-4-methoxybenzoyl]-N2-(4-methoxybenzoyl)-1,2-benzenediamine

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Reaction Steps

The free base form of N1-[2-(2-aminoethoxy)-4-methoxybenzoyl]-N2-(4-methoxybenzoyl)-1,2-benzenediamine was prepared by vigorously stirring N1-[2-(2-aminoethoxy)-4-methoxybenzoyl]-N2-(4-methoxybenzoyl)-1,2-benzenediamine trifluoroacetate (1.88 g, 3.42 mmol) with 100 ml water, 2 grams potassium carbonate and 100 ml of CH2Cl2 for several hours at room temperature. After stirring, the organic layer was set aside and combined with a 150 ml CH2Cl2 wash of the original aqueous layer. The combined CH2Cl2 extracts were washed with brine, dried over Na2SO4, concentrated in vacuo, then purified on a chromatotron system (4 mm plate) with 9:1 CH2Cl2:MeOH eluent to provide N1-[2-(2-aminoethoxy)-4-methoxybenzoyl]-N2-(4-methoxybenzoyl)-1,2-benzenediamine (1.26 g, 85%) as a brittle white foam after high vacuum drying.

Provenance & Evidence