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

HRID 1614435Notes

Reaction equation

HRID 1614435 reaction equation
[C:1]1([CH:7]=[N:8][C:9]2[CH:14]=[CH:13][C:12](N=CC3C=CC=CC=3)=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(COC2C=CC=CC=2)C=CC=CC=1.[CH2:37]([N:44]([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C(OCC)(=O)C>[C:51]1([N:44]([CH2:37][C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:45]2[CH:46]=[CH:47][C:48]([N:8]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:49][CH:50]=2)[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1

Participants

5

Reactant 3

HCID 69080BenzyldiphenylamineHCID 70352Benzyl Phenyl EtherHCID 272373N1,N4-Dibenzylidenebenzene-1,4-diamine

Product 1

HCID 15701549N,N'-Dibenzyl-N,N'-diphenyl-p-phenylenediamine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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.

Sources & evidence

ORD record
ord-ea6741311d144813ba9355292035e0bc
Source dataset
uspto-grants-1993_03
Patent number
US05196606

Reaction notes

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