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

Safety Information

Risk Statements 

20/21/22

Safety Statements 

3/9-36/37

HS Code 

29339900

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(24666-56-6)Related Product Information

• Methyl 2-(chloromethyl)-3-nitrobenzoate
• 4-[(4-Chlorophenyl)-2-pyridinylmethoxy]-1-piperidinecarboxylic acid ethyl ester
• N-Acetyl Lenalidomide
• cis-1,2,3,6-Tetrahydrophthalic anhydride
• Argatroban
• Bumetanide
• Citalopram
• Methyl 2-bromomethyl-5-nitrobenzoate
• Lenalidomide Impurity 13
• Lenalidomide Impurity 11
• (3R,5R)-3-(Boc-amino)-5-methylpiperidine
• Lenalidomide Impurity 3
• tert-butyl N-[(3R,5S)-5-methylpiperidin-3-yl]carbamate
• Lenalidomide Impurity 14
• Lenalidomide Impurity 12
• Lenalidomide Impurity 7
• Lenalidomide Impurity (2)
• Lenalidomide Glucosides