A Bis(phosphaethenyl)pyridine Complex of Iridium(I): Synthesis and Catalytic Application to N-Alkylation of Amines with Alcohols was written by Chang, Yung-Hung;Nakajima, Yumiko;Ozawa, Fumiyuki. And the article was included in Organometallics in 2013.Name: 4-(Benzylamino)benzonitrile This article mentions the following:
The Ir(I) complex [IrCl(BPEP-H)] (1), coordinated with 2,6-bis[2-(2,4,6-tri-tert-butylphenyl)-2-phosphaethenyl]pyridine (BPEP-H) as a PNP-pincer-type phosphaalkene ligand, was synthesized and fully characterized by elemental anal., NMR spectroscopy, and x-ray diffraction anal. Complex 1 (1 mol %) catalyzes N-alkylation of primary and secondary amines with alcs., leading to the selective formation of secondary and tertiary amines, resp. Primary amines are smoothly alkylated with a variety of benzylic and aliphatic alcs. (1 or 3 equiv) at 100° under basic conditions (CsOH, 10 mol %) to give the corresponding secondary amines in good to high yields. However, N-alkylation of secondary amines with benzyl alc. (3 equiv) proceeds in the presence of KH2PO4 (5 mol %) at 140° to afford tertiary amines in high yields. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Name: 4-(Benzylamino)benzonitrile).
4-(Benzylamino)benzonitrile (cas: 10282-32-3) belongs to nitriles. Nitrile compounds can be prepared by the incorporation of a cyanide source through C–C bond formation or by dehydration of primary carboxamides. Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.Name: 4-(Benzylamino)benzonitrile
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts