With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.10315-07-8,1-Benzylpiperidine-4-carboxylic acid,as a common compound, the synthetic route is as follows.
General procedure: A 20 mL Radleys Carousel screw-capped glass tube was charged with carboxylic acid (2 mmol, 1.0 equiv), DMF (1.2 mL), T3P in DMF 50%(1.28 mL, 1.4 g, 1.1 equiv) and HCl (4 M in dioxane, 0.25 mL, 1.0mmol, 0.5 equiv) at r.t. The mixture was heated to 130 C (ca. 120 C internal) and stirred until the conversion according to LC-MS or TLCwas ?95%. The solution was quenched at 10 C with aq half-saturated Na2CO3 (5 mL; caution: gas evolution) and extracted with i-PrOAc (10mL and 2 ¡Á 5 mL or until no product was present in the aqueousphase). Combined organic phases were dried over MgSO4 and concentratedunder reduced pressure. The crude product was purified bychromatography on silica gel as described below. 1-Benzyl-N,N-dimethylpiperidine-4-carboxamide (17)The reaction was performed according to the general procedure with1-benzylpiperidine-4-carboxylic acid as starting material. Afterwork-up, the crude material was absorbed on Celite, concentrated todryness and purified by chromatography on silica gel (5 g Isolute SPEcolumn, Flash Si II; heptane-EtOAc, 4:1 to 1:9) to give 17.Yield: 450 mg (91%) yellow solid; mp 83.5-84.5 C.IR: 2926 (m), 1730 (w), 1635 (s), 1493 (m), 1341 (m), 1266 (m), 1139(m), 997 (m), 789 (w) cm-1. 1H NMR (500 MHz, CDCl3): delta = 7.31-7.35 (m, 4 H), 7.23-7.28 (m, 1 H),3.53 (s, 2 H), 3.05 (s, 3 H), 2.95 (m, 5 H), 2.49 (tt, J = 3.7, 11.4 Hz, 1 H),2.02 (t, J = 11.4 Hz, 2 H), 1.85-1.93 (m, 2 H), 1.68 (d, J = 12.9 Hz, 2 H).13C NMR (125 MHz, CDCl3): delta = 175.09, 138.45, 129.09, 128.19,126.96, 63.27, 53.21, 38.93, 37.06, 35.61, 28.53.MS: m/z = 247.16 [M + 1]+.HRMS (ESI): m/z [M + H]+ calcd for C15H22N2O: 247.1805; found:247.1809., 10315-07-8
10315-07-8 1-Benzylpiperidine-4-carboxylic acid 4714983, apiperidines compound, is more and more widely used in various.
Reference£º
Article; Bannwart, Linda; Abele, Stefan; Tortoioli, Simone; Synthesis; vol. 48; 13; (2016); p. 2069 – 2078;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem