Sugasawa, Shigehiko published the artcileSynthesis of piperidine derivatives, Safety of (1-Methylpiperidin-3-yl)methanamine, the publication is Yakugaku Zasshi (1956), 968-70, database is CAplus.
4-MeO2CC5H4N (60 g.) and 60 ml. 28% NH4OH at 0° saturated with NH3 gas, kept overnight and the product recrystallized from EtOH gave 44.2 g. 4-H2NOCC5H4N (I), m. 152-5°. I or 3-H2NCOC5H4N (10 g.), 17.5 g. MeI, and 30 ml. MeOH refluxed 5 hrs., the MeI and MeOH removed in vacuo, the residue in 30 ml. water converted to its acid chloride by usual method, reduced with PtO2 and H until absorption of 3 moles H, and the product concentrated and recrystallized from EtOH yielded about 85% 1,x-Me(H2NOC)C5H9N.HCl (II, x = 3, m. 232°; x = 4, hygroscopic). II (7 g.) and 7 g. P2O5 heated 3 hrs. at 160-80°, cooled, 50 ml. water added, neutralized with K2CO3 and the product extracted with AcOEt yielded about 80% 1,x-Me(NC)C5H9N (III, x = 3, b20 95-6°; x = 4, b21 97°). LiAlH4 (1.3 g.) and 150 ml. Et2O at 0° treated dropwise with 5 g. III in 50 ml. Et2O, stirred 1.5 hrs., refluxed 30 min., cooled, 15 ml. water added, the precipitate filtered off, treated with 50 ml. 20% Rochelle salt solution, extracted with Et2O, the Et2O layer and the Et2O extract combined and distilled yielded about 90% 1,x-Me(H2NCH2)C5H9N {IV, x = 3, b20 81-2° [dipicrate, m. 231° (decomposition)]; x = 4, b20 80-1° [dipicrate, m. 236° (decomposition)]}. KOH (32 g.) in 400 ml. water treated with 6.4 g. Br, the solution at 0° treated with 5.7 g. II in a small amount of water, heated 1 hr. at 70°, made strongly alk. with KOH, the product steam distilled into dilute HCl, the solution concentrated, made alk. with KOH and extracted with Et2O yielded about 65% 1,x-Me(H2N)C5H9N {V, x = 3, b43 74-5° [dipicrate, m. 277° (decomposition)]; x = 4, b35, 70-1° [dipicrate, m. 263° (decomposition)]}. R2NH (0.6 mole) in 200 ml. PhMe poured dropwise into 50% COCl2, refluxed 1 hr. and the product distd, yielded 71% R2NCOCl (VI, R = Me, b55-60 85-8°; R = Et, b17-20 80°). IV or V (2 moles) and 1 mole VI in Et2O mixed at 0°, let stand 1.5 hrs. at room temperature, refluxed 10 min., the solution filtered and the filtrate concd, gave 1,x-Me[R2NCONH(CH2)n]C5H9N (x, n, R, and m.p. given): 4, 1, Me, 40-4° [HCl salt, 230° (decomposition)]; 4, 1, Et, 66-8°; 4, 0, Me, 138-9°; 4, 0, Et, 89-90°; 3, 1, Me, 66-9°; 3, 1, Et, -(sirup); 3, 0, Me, 110-2°; 3, 0, Et, -(sirup) (picrolonate, m. 195-7°).
Yakugaku Zasshi published new progress about 14613-37-7. 14613-37-7 belongs to piperidines, auxiliary class Piperidine,Amine, name is (1-Methylpiperidin-3-yl)methanamine, and the molecular formula is C17H16O2, Safety of (1-Methylpiperidin-3-yl)methanamine.
Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem