Chichibabin, A. E. published the artcileAction of aldehydes on α-aminopyridine and on α-dimethylaminopyridine, Related Products of ethers-buliding-blocks, the publication is Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1931), 2839-42, database is CAplus.
In the action of HCHO on α-aminopyridine (1), 2 reactions take place simultaneously, condensation to a dipyridyl derivative and methylation of the amino group, the end product being p,p’-tetra methyldiaminodipyridylmethane (C. A. 24, 1642). It seemed of interest to study the behavior of other aldehydes toward I under these conditions. With aromatic aldehydes in HCO2H there is no condensation, only a reaction analogous to the above methylation but differing from it in that only 1 H atom of the amino group seems to be replaced by the aromatic residue because the primarily formed Schiff base is at once reduced; secondary amines can be obtained in excellent yield by this method. The o-substituted derivatives of BzH studied (o-NO2, o-HO) do not react with I under these conditions. BzH, heated with α-C5H4NNMe2 (II) and ZnCL2, reacts like BzH with PhNMe2, giving phenylbis(α-dimethylaminopyridyl)methane (III), which is oxidized by PbO2 in acid solution to the carbinol (IV). α-Benzylaminopyridine, m. 94°, is obtained in 90% yield from I in anhydrous HCO2H refluxed with BzH. α-(p-Methoxybenzylamino)pyridine, from I and anisaldehyde (80-5% yield), m. 128°. α-(3,4-Methylenedioxybenzylamino)-pyridine (70%), m. 99-100°. α-Formylaminopyridine, from equimol. amounts of I and anhydrous HCO2H carefully heated in a Claisen flask until the formation of water ceased, b15161-2°, m. 71°. III (6 g. from 10 g. II), m. 130-1°, soluble in H2SO4 without color. IV, yellowish, m. 123-4°, soluble in concentrated H2SO4 with blood-red and in HCl with deep red color, water destroying the color, which, however, is restored by concentrated acids, although the simple salts cannot be obtained in colored form.
Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen published new progress about 52818-63-0. 52818-63-0 belongs to ethers-buliding-blocks, auxiliary class Pyridine,Amine,Benzene,Ether, name is N-(4-Methoxybenzyl)pyridin-2-amine, and the molecular formula is C13H14N2O, Related Products of ethers-buliding-blocks.
Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem