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| | 2,6-Dioxopiperidine-3-ammonium chloride Basic information | | Description |
| Product Name: | 2,6-Dioxopiperidine-3-ammonium chloride | | Synonyms: | 2,6-Dioxopiperidine-3-ammonium chloride;2,6-Piperidinedione, 3-amino-, hydrochloride;Glutamic acid imide hydrochloride;3-Amino-2,6-dioxo-piperidine hydrochloride ,99%;3-AMino-2,6-Piperidinedione HCl;3-AMino-2,6-dioxo-piperidine hydrochloride;2,6-Piperidinedione,3-aMino-, hydrochloride (1:1);3-amino piperdine-2,6-dion hydrochloride | | CAS: | 24666-56-6 | | MF: | C5H9ClN2O2 | | MW: | 164.59016 | | EINECS: | 807-866-6 | | Product Categories: | Pyrrolidines;24666-56-6 | | Mol File: | 24666-56-6.mol |  |
| | 2,6-Dioxopiperidine-3-ammonium chloride Chemical Properties |
| Melting point | 120 °C (approx) | | storage temp. | Inert atmosphere,Room Temperature | | solubility | DMSO (Slightly, Heated), Methanol (Sparingly, Sonicated) | | form | powder | | color | White | | InChI | InChI=1S/C5H8N2O2.ClH/c6-3-1-2-4(8)7-5(3)9;/h3H,1-2,6H2,(H,7,8,9);1H | | InChIKey | YCPULGHBTPQLRH-UHFFFAOYSA-N | | SMILES | C1CC(N)C(=O)NC1=O.Cl |
| | 2,6-Dioxopiperidine-3-ammonium chloride Usage And Synthesis |
| Description | 2,6-Dioxopiperidine-3-ammonium chloride is a reagent for preparing lenalidomide that can induce ubiquitination and degradation of CK1α in del (5q) MDS. It can also be used to prepare phthalimide conjugates that can promote ligand-dependent target protein degradation. Moreover, it is also a metabolite of thalidomide (T338850) that inhibits FGF-induced angiogenesis.
| | Chemical Properties | White crystal | | Uses | 2,6-Dioxopiperidine-3-ammonium chloride can be used as an important intermediate of antineoplastic drug lenalidomide. | | Synthesis | General procedure for the synthesis of 3-aminopiperidine-2,6-dione hydrochloride from benzyl (2,6-dioxopiperidin-3-yl)carbamate: Benzyl (2,6-dioxopiperidin-3-yl)carbamate (4.00 g, 15.0 mmol) was dissolved in methanol (200 mL) and 2N HCl solution (15 mL) was added. Subsequently, 5% Pd-C catalyst (100 mg) was added and the hydrogenation reaction was carried out at 60 psi hydrogen pressure for 4 hours. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated to dryness to afford 3-aminopiperidine-2,6-dione hydrochloride as a white solid (2.61 g, 100% yield) with a melting point of 245 °C (decomposition, ignition temperature 235 °C).1H NMR (400 MHz, DMSO-D6) δ ppm: 11.22 (br s, 1H), 8.68 (br s, 3H), 4.20 (dd, J = 13.0, 5.3 Hz, 1H), 2.77-2.65 (m, 1H), 2.64-2.56 (m, 1H), 2.27-2.19 (m, 1H), 2.09-1.97 (m, 1H). | | References | [1] Patent: WO2008/7979, 2008, A1. Location in patent: Page/Page column 13
[2] Patent: CN108218833, 2018, A. Location in patent: Paragraph 0043; 0044; 0057; 0058; 0063; 0071; 0072
[3] Patent: WO2018/154516, 2018, A1. Location in patent: Page/Page column 7-8
[4] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 11, p. 1625 - 1630 |
| | 2,6-Dioxopiperidine-3-ammonium chloride Preparation Products And Raw materials |
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