With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.20691-89-8,1-Methyl-4-piperidinemethanol,as a common compound, the synthetic route is as follows.
Example 24 1-Methyl-4-(4-nitrophenoxymethyl)piperidine (24): A mixture of 1-chloro-4-nitrobenzene (23) (2.37 g, 15.0 mmol), alcohol 22 (1.94 g, 15.0 mmol), and DMSO (25 mL) was treated portionwise with NaH (60% in mineral oil, 660 mg, 16.5 mmol) at 40 C. The mixture was stirred at 70 C. for 3 h, poured into water (150 mL), and extracted with Et2O (5*100 mL). The combined organic fractions were washed with water (250 mL) and brine (250 mL), dried (MgSO4), and the solvent was removed in vacuo. The resulting solid was recrystallized from Et2O to give 24 (3.12 g, 83%) as yellow needles. 1H NMR (300 MHz, CDCl3): delta=1.36-1.56 (m, 2H, 3-Hax, 5-Hax), 1.75-1.91 (m, 3H, 3-Heq, 4-H, 5-Heq), 1.98 (dt, J=11.9, 1.9 Hz, 2H, 2-Hax, 6-Hax), 2.30 (s, 3H, NMe), 2.85-2.98 (m, 2H, 2-Heq, 6-Heq), 3.90 (d, J=5.8 Hz, 2H, OCH2), 6.94 (mc, 2H, 2′-H, 6′-H), 8.19 (mc, 2H, 3′-H, 5′-H) ppm. -13C NMR (50.3 MHz, CDCl3): delta=28.9 (C-3, C-5), 35.1 (C-4), 46.4 (NMe), 55.3 (C-2, C-6), 73.3 (OCH2), 114.3 (C-2′, C-6′), 125.8 (C-3′, C-5′), 141.3 (C-4′), 164.1 (C-1′) ppm. -MS (70 eV, EI): m/z (%)=250 (79) [M]+, 249 (100) [M-H]+. -C13H18N2O3 (250.29): calcd. C, 62.38; H, 7.25; found C, 62.25; H, 7.40., 20691-89-8
As the paragraph descriping shows that 20691-89-8 is playing an increasingly important role.
Reference：
Patent; Beusker, Patrick Henry; De Groot, Franciscus Marinus Hendrikus; Tietze, Lutz F.; Major, Felix; Joosten, Johannes Albertus Frederikus; Spijker, Henri Johannes; US2009/318668; (2009); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem