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

Participants

Reaction Steps

Chloro-4-(phenylmethoxy)benzene (2.18 g, 0.010 mol) and N-(phenylmethylene)benzenamine (1.81 g, 0.010 mol) were reacted 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 things 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.

Provenance & Evidence