21319-53-9 | Heterocyclic Building Blocks-piperidine

Seo, Hyowon et al. published their research in Nature Chemistry in 2017 | CAS: 21319-53-9

1-Benzylpiperidine-2-carboxylic acid (cas: 21319-53-9) belongs to piperidine derivatives. Piperidine is a saturated organic heteromonocyclic parent, an azacycloalkane, a secondary amine and a member of piperidines. Industrially, piperidine is produced by the hydrogenation of pyridine, usually over a molybdenum disulfide catalyst. Pyridine can also be reduced to piperidine via a modified Birch reduction using sodium in ethanol.Synthetic Route of C13H17NO2

Photoredox activation of carbon dioxide for amino acid synthesis in continuous flow was written by Seo, Hyowon;Katcher, Matthew H.;Jamison, Timothy F.. And the article was included in Nature Chemistry in 2017.Synthetic Route of C13H17NO2 This article mentions the following:

Although carbon dioxide (CO₂) is highly abundant, its low reactivity has limited its use in chem. synthesis. In particular, methods for carbon-carbon bond formation generally rely on two-electron mechanisms for CO₂ activation and require highly activated reaction partners. Alternatively, radical pathways accessed via photoredox catalysis could provide new reactivity under milder conditions. Here we demonstrate the direct coupling of CO₂ and amines via the single-electron reduction of CO₂ for the photoredox-catalyzed continuous flow synthesis of 伪-amino acids. By leveraging the advantages of utilizing gases and photochem. in flow, a com. available organic photoredox catalyst effects the selective 伪-carboxylation of amines that bear various functional groups and heterocycles. The preliminary mechanistic studies support CO₂ activation and carbon-carbon bond formation via single-electron pathways, and we expect that this strategy will inspire new perspectives on using this feedstock chem. in organic synthesis. In the experiment, the researchers used many compounds, for example, 1-Benzylpiperidine-2-carboxylic acid (cas: 21319-53-9Synthetic Route of C13H17NO2).

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Brief introduction of 21319-53-9

21319-53-9, The synthetic route of 21319-53-9 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.21319-53-9,1-Benzylpiperidine-2-carboxylic acid,as a common compound, the synthetic route is as follows.

General procedure: The fragment carboxylic acid (0.35 mmol) was dissolved in dimethylformamide (0.2 M, 1.75 mL), then 14 (42.6 mg, 0.35 mmol), HBTU (128 mg, 0.34 mmol), and HOBT (51.8 mg, 0.38 mmol) were added, followed by diisopropylethylamine (175 muL, 1.047 mmol). The reaction was stirred at 23 C for 16 h. TLC at 16 h showed conversion to product. The reaction was quenched with H2O (5 mL) and extracted with DCM (3 x 5 mL). The combined organic layers were washed with 1 M HCl (10 mL), saturated aqueous NaHCO3 (10 mL), and saturated aqueous NaCl (10 mL). The organic layer was dried over MgSO4, filtered, and evaporated. Purification with flash column chromatography with CH3OH/CH2Cl2 ( CH3OH gradient 0 ? 5 %).

21319-53-9, The synthetic route of 21319-53-9 has been constantly updated, and we look forward to future research findings.

Reference：
Article; McShan, Danielle; Kathman, Stefan; Lowe, Brittiney; Xu, Ziyang; Zhan, Jennifer; Statsyuk, Alexander; Ogungbe, Ifedayo Victor; Bioorganic and Medicinal Chemistry Letters; vol. 25; 20; (2015); p. 4509 – 4512;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

Some tips on 21319-53-9

21319-53-9, 21319-53-9 1-Benzylpiperidine-2-carboxylic acid 2841641, apiperidines compound, is more and more widely used in various fields.

21319-53-9, 1-Benzylpiperidine-2-carboxylic acid is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 5 1,3,4,11a-Tetrahydro-2H-benzo[b]quinolizin-11(6H)-one. The following is a modification of the procedure reported (Gonzalez Trigo, G.; Alvarez-Builla, J. An. Quim., Ser. C 1980, 76, 12). N-benzylpipecolinic acid (5.10 g, 20.0 mmol) was placed in a 500 mL flask. Polyphosphoric acid (200 g) was added. The mixture was heated in an oil bath gradually to 140 C. with stirring. It was stirred at 140 C. until the bubbling stopped, then cooled to room temperature and poured into ice. The mixture was neutralized with aqueous NaGH (40%) and extracted with ether (5*80 mL). The combined extracts were washed with brine, dried (Na2SO4) and concentrated in vacuo to give a red solid (3.08 g, 77%): m.p. 71-72 C. (benzene); 1H NMR (300 MHz) delta 8.02 (dd, J=7.8, 1.3 Hz, 1 H), 7.50 (td, J=7.3, 1.4 Hz, 1 H), 7.35 (t, J=7.6 Hz, 1 H), 7.23 (d, J=7.6 Hz, 1 H), 3.88 (d, J=15.2 Hz, H-6), 3.68 (d, J=14.9 Hz, H-6), 3.09 (br d, J=11.2 Hz, 1 H), 2.77 (br d, J=10.5 Hz, 1 H), 2.44 (m, 1 H), 2.35 (td, J=11.3, 3.5 Hz, 1 H), 1.90 (br d,J=12.5 Hz, 1 H), 1.32-1.76 (m, 4 H); 13C NMR (75 MHz) delta 195.87, 141.73, 133.53, 130.12, 127.34, 127.00, 126.17, 69.21, 57.14, 56.13, 26.66, 25.02, 23.81.

21319-53-9, 21319-53-9 1-Benzylpiperidine-2-carboxylic acid 2841641, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; American Biogenetic Sciences, Inc.; University College Dublin; US6436954; (2002); B1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem