Triethylamine → N-7-Phenylheptyl-3,5-bis-(3,5-dimethylphenyl)-4-methoxymethoxybenzamide

Participants

Reaction Steps

A flamed dried round bottom flask was charged with 7-phenylheptyl amine (354 mg, 2.78 mmol) and 20 mL anhydrous CH2Cl2. To this solution was added 3,5-bis-(3,5-dimethylphenyl)-4-methoxymethoxybenzoic acid (780 mg, 1.85 mmol), triethyl amine (563 mg, 5.56 mmol, 726 μL), anhydrous 1-hydroxybenzotriazole (275 mg, 2.04 mmol), and DCC (459 mg, 2.22 mmol), all at room temperature. The reaction mixture was stirred at room temperature for one-half hour. Then the reaction was worked up by adding water then extracting with EtOAc (3×). The combined organic extracts were dried over Na2SO4 and the solvent removed in vacuo to give a semisolid to which CH2Cl2 was added. This suspension was subjected to column chromatography (15% EtOAc: 85% Hexanes) to give 600 mg, 54.5% of the amide as a colorless oil. 1H NMR (CDCl3) δ 1.34 (bs, 6H); 1.57 (m, 4H); 2.36 (s, 12H); 2.572 (t, J=8.18 Hz, 2H); 2.681 (s, 3H); 3.414 (quartet, J=8.18 Hz, 2H); 4.39 (s, 2H); 6.04 (t, J=5.73 Hz, 1H); 6.97 (s, 2H); 7.12–7.27 (m, 9H); 7.67 (s, 2H).

Provenance & Evidence