Hirao, Ichiro published the artcileCondensation of anisyl alcohol or benzyl alcohol with aromatic amines, Synthetic Route of 52818-63-0, the publication is Yakugaku Zasshi (1954), 853-5, database is CAplus.
A mixture of 7 g. p-MeOC6H4CH2OH (I), 5 g. 2-aminopyridine (II), 20 g. xylene, and 4 g. KOH refluxed 21 hrs., extracted with 10% HCl, KOH added to pH 7, and the product recrystallized from dilute MeOH give 8.9 g. (80%) 2-(p-methoxybenzylamino)pyridine (III), m. 108°, or 5.5 g. I, 3.5 g. II, 8 g. PhMe, and 4 g. KOH refluxed 12 hrs. and the product treated as above give 4.8 g. (62%) III, m. 123-4°. I (7 g.), 4.7 g. PhNH2, 20 g. xylene, and 4 g. KOH refluxed 21 hrs., and the product precipitated with 10% HCl, dissolved in KOH, and recrystallized from MeOH gives 5 g. (51%) p-MeOC6H4CH2NHPh, m. 63-4°. Similarly, 20 g. PhCH2OH, 6 g. 2-aminopyrimidine, 40 g. PhMe, and 7 g. KOH refluxed 10 hrs. give 16 g. (44%) 2-benzylaminopyrimidine, m. 79-81°; 8 g. PhCH2OH, 6 g. 2-H2NC5H4N, 4 g. PhMe, and 15 g. PhMe refluxed 13 hrs. give 11 g. (81%) 2-PhCH2NHC5H4N, m. 95-6°; 10.8 g. PhCH2OH, 9.3 g. PhNH2, 40 g. xylene, and 8 g. KOH refluxed 21 hrs. give 1.47 g. PhCH2NHPh.HCl, m. 214-5°.
Yakugaku Zasshi 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, Synthetic Route of 52818-63-0.
Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem