Benzyldiphenylamine → N,N'-Dibenzyl-N,N'-diphenyl-p-phenylenediamine

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Reaction Steps

N,N'-Bis(phenylmethylene)benzene-1,4-diamine (1.42 g, 0.005 mol) and phenylmethoxybenzene (1.84 g, 0.010 mol) were heated in Na/DMF (1 g: 50 mL) at 100° C. for 1 hr. Similar workup as for the preparation of benzyldiphenylamine and chromatography on silica using petroleum ether/chloroform 4:1 as eluent gave 0.35 g (16%) mp 149°-51° C. from ethyl acetate. 1H NMR (200 MHz, CDCl3) δ (assignment): 4.96 (s, 4H, PhCH2N-), 6.80-6.97 (m, 6H, aromatic), 7.05 (s, 4H, (PhCH2 (Ph)N)2C6II4), 7.16-7.33 (m, 14H, aromatic). MS [m/e (70 eV, % of base peak)] (PhCH2 (Ph)N)2C6H4 440 (M+., 25.4), 349 (M+. -C7H7., 24.5), 91 (C7H7+, 100). HRMS (m/z) for C32H28N2 (M+.) calcd. 440.225, found 440.227.

Provenance & Evidence