N-Benzylideneaniline → N-(4-Chlorophenyl)-N-phenyl-benzenemethanamine

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Chloro-4-(phenylmethoxy)benzene (2.18 g, 0.010 mol) and N-(phenylmethylene)benzenamine (1.81 g, 0.010 mol) were reated in Na/DMF (1 g: 50 mL) at 50° C. for 7 hrs. The reaction was followed by HPLC to about 90% conversion. This technique indicated among other thigs the presence of the title compound, benzyldiphenylamine, and some unknown material in a ratio 65:18:17. Similar aqueous workup as for the preparation of benzyldiphenylamine and chromatography on silica gave 0.50 g of the title compound mp 94°-5° C. from methanol (lit8 mp 97°-7.5° C. 70% yield). This material is contaminated with a small amount of diphenylbenzylamine. 1H NMR (200 MHz, CDCl3) δ (assignment): 5.03 (s, 2H, Ph2NCH2Ph), 6.96-7.38 (m, 14H, aromatic). MS [m/e (70 eV, % of base peak)] C19H16ClN 293 (M+., 52.8), 295 (M+. +2, 28.8), 202 (M+. -C7H7+, 22), 167(C6H4NPh)+., 48.3), 91 (C7H7+, 100). FTIR (CDCl3): 3066, 3033, 1589, 1494, 1454 cm-1.

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