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

HRID 1614434Notes

Reaction equation

[Cl:1]C1C=CC(OCC2C=CC=CC=2)=CC=1.C1(C=NC2C=CC=CC=2)C=CC=CC=1.[CH2:30]([N:37]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>>[Cl:1][C:47]1[CH:48]=[CH:49][C:44]([N:37]([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[CH:45][CH:46]=1

Participants

Reactant 3

HCID 10858N-Benzylideneaniline

HCID 69080Benzyldiphenylamine

HCID 139062Benzene, 1-chloro-4-(phenylmethoxy)-

Product 1

HCID 12229151N-(4-Chlorophenyl)-N-phenyl-benzenemethanamine

Procedure

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.

Sources & evidence

ORD record: ord-07ef1bb4dbf44674b3e2ee985944aabc
Source dataset: uspto-grants-1993_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05196606

Reaction notes

Loading…