| Identification | Back Directory | [Name]
2,6-Dioxopiperidine-3-ammonium chloride | [CAS]
24666-56-6 | [Synonyms]
Pomalidomide Impurity 6
Lenalidomide Impurity 6
6-piperidinedione hydrochloride
3-AMino-2,6-Piperidinedione HCl
Glutamic acid imide hydrochloride
2-Amino-glutarimide Hydrochloride
DL-Glutamic Acid Imide Hydrochloride
2,6-dioxopiperidin-3-aminium chloride
2,6-Dioxopiperidine-3-ammonium chloride
3-amino piperdine-2,6-dion hydrochloride
3-Amino-2,6-piperidinedione hydrochloride
3-AMino-2,6-dioxo-piperidine hydrochloride
3-Aminopiperidine-2,6-dione Monohydrochloride
2,6-Piperidinedione, 3-amino-, hydrochloride
3-Amino-2,6-dioxo-piperidine hydrochloride ,99%
2,6-Piperidinedione,3-aMino-, hydrochloride (1:1)
2,6-Dioxopiperidine-3-ammonium chloride###3-aminopiperidine-2,6-dione hydrochloride | [EINECS(EC#)]
2017-001-1 | [Molecular Formula]
C5H9ClN2O2 | [MDL Number]
MFCD11042437 | [MOL File]
24666-56-6.mol | [Molecular Weight]
164.59 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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 |
| Questions And Answer | Back Directory | [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.
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