Triethylamine → N-[4-methoxy-3-(naphthylmethoxy)phenyl]-2-naphthylethanamide

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Reaction Steps

N-[4-methoxy-3-(naphthylmethoxy)phenyl]-2-naphthylethanamide (Exemplary Compound 48) was prepared using the same experimental conditions used to prepare Exemplary Compound 52 (Scheme X, above). From 4-methoxy-3-(2-naphthylethoxy)phenylamine (350 mg, 1.25 mmol) and 1-naphthylacetyl chloride (260 mg, 1.25 mmol) in 10 mL of dimethyl acetamide containing triethylamine (1 mL, 7.17 mmol) stirred at room temperature for 16 h., was obtained 370 mg of product in (66%) yield as off white needles after recrystallization from ethyl acetate/hexane: mp 161-163° C. 1H NMR (400 MHz, Me2SO-d6) δ3.69 (s, 3H); 4.11 (s, 2H); 5.45 (s, 2H); 6.93 (d, 1H, J=8.8); 7.18 (dd, 1H, J=2.3, 8.7); 7.46-7.64 (m, 9H); 7.82-8.15 (m, 6H); 10.20 (s, 1H). Anal. Calcd for C30H25NO3: C, 80.51; H, 5.63; N, 3.13. Found: C, 80.38; H, 5.70; N, 3.12.

Provenance & Evidence