2,6-Dioxopiperidine-3-ammonium chloride

Base Information

• Chemical Name: 2,6-Dioxopiperidine-3-ammonium chloride
• CAS No.: 24666-56-6
• Molecular Formula: C5H9ClN2O2
• Molecular Weight: 164.592
• Hs Code.: 29339900
• Mol file: 24666-56-6.mol

Synonyms:2,6-Piperidinedione,3-amino-, monohydrochloride (9CI);Glutarimide, 2-amino-, hydrochloride(6CI,7CI);Glutarimide, 2-amino-, monohydrochloride (8CI);3-Amino-2,6-dioxopiperidine hydrochloride;3-Aminopiperidine-2,6-dione monohydrochloride;DL-Glutamic acidimide hydrochloride;Glutamimide hydrochloride;

Chemical Property of 2,6-Dioxopiperidine-3-ammonium chloride

Chemical Property:

• Vapor Pressure: 0.000128mmHg at 25°C
• Melting Point: 120 °C (approx)
• Boiling Point: 334.5 °C at 760 mmHg
• Flash Point: 156.1 °C
• PSA: 72.19000
• LogP: 0.58140
• Storage Temp.: Inert atmosphere,Room Temperature

Purity/Quality:

99.9% ^*data from raw suppliers

3-Aminopiperidine-2,6-dioneHydrochloride ^*data from reagent suppliers

Safty Information:

• Statements: 20/21/22
• Safety Statements: 3/9-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Uses and Mechanism of Action: Prostate Cancer Treatment:; Inhibits prostate cancer cell growth.; ; Inhibition of DNA Synthesis:; Blocks DNA synthesis by inhibiting the enzyme benzoate.; ; Inhibition of Pomalidomide Synthetase:; Potently inhibits the enzyme pomalidomide synthetase.
• Production Methods: Synthesized through chemical reactions involving the reaction of 3-aminopiperidine-2,6-dione with hydrochloric acid.
• Analysis Method: Characterized using analytical techniques such as Fourier-transform infrared spectroscopy (FT-IR), proton nuclear magnetic resonance spectroscopy (1H NMR), and carbon-13 nuclear magnetic resonance spectroscopy (13C NMR) to analyze the chemical structure and composition of 3-Aminopiperidine-2,6-dione hydrochloride.
• References: [1] Discovery of a Small-Molecule Degrader of Bromodomain and Extra-Terminal (BET) Proteins with Picomolar Cellular Potencies and Capable of Achieving Tumor Regression; DOI 10.1021/acs.jmedchem.6b01816; [2] Experimental design optimization for the synthesis of lenalidomide nitro precursor; DOI 10.1007/s11164-022-04869-5; [3] Design, synthesis, and biological evaluation of a novel series of 2-(2,6-dioxopiperidin-3-yl)isoquinoline-1,3(2H,4H)-dione derivatives as cereblon modulators; DOI 10.1080/14756366.2022.2087219

Technology Process of 2,6-Dioxopiperidine-3-ammonium chloride

There total 10 articles about 2,6-Dioxopiperidine-3-ammonium chloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine (24666-55-5,179915-11-8) → rac-α-aminoglutarimide hydrochloride (24666-56-6,2686-86-4)

Guidance literature:

With hydrogenchloride; hydrogen; 5% palladium over charcoal; In methanol; water; for 4h; under 3102.97 Torr;

Reference yield: 99.0%

(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester (31140-42-8) → rac-α-aminoglutarimide hydrochloride (24666-56-6,2686-86-4)

Guidance literature:

With hydrogenchloride; In methanol; water; for 2h;

DOI:10.1039/d0cc05395c

Reference yield: 96.0%

N-(2,6-dioxopiperidin-3-yl)-2-phenylacetamide (77658-84-5) → rac-α-aminoglutarimide hydrochloride (24666-56-6,2686-86-4)

Guidance literature:

With hydrogenchloride; hydrogen; palladium 10% on activated carbon; In methanol; for 23h; under 760.051 Torr;

upstream raw materials:

3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine

Cbz-L-Gln

N-benzyloxycarbonyl-L-isoglutamine

N-(2,6-dioxopiperidin-3-yl)-2-phenylacetamide

Downstream raw materials:

2-(2,6-dioxo-3-piperidinyl)-5-nitro-1H-isoindole-1,3(2H)-dione

4-NT

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

2-amino-N-(2,6-dioxopiperidin-3-yl)-6-methylbenzamide

Refernces

• 1、 -. "Synthesis method of pomalidomide intermediate". Paragraph 0009; 0028-0043. . Retrieved 2020/09/30.
• 2、 -. "A method for the preparation of amine to that (by machine translation)". Paragraph 0043; 0044; 0057; 0058; 0063; 0071; 0072. . Retrieved 2018/07/30.