- Piperidine-2,4-dione
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- $200.00
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2026-09-02
- CAS:50607-30-2
- Min. Order: 1KG
- Purity: 99%, 99.5% Sublimated
- 2,4-PiperadinedioneE
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- $1.00
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2019-07-06
- CAS:50607-30-2
- Min. Order: 1KG
- Purity: 97%
- Supply Ability: 200KG
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| | 2,4-Piperadinedione Basic information |
| Product Name: | 2,4-Piperadinedione | | Synonyms: | piperidine-2,4-dione, dihydropyridine-4,6-dione, 2,4-dioxopiperidine, 2,4-piperidinedione, piperidin-2,4-dione, 2,4-diketopiperidine, Piperidine-2,4-dione;2,4-PiperadinedioneE;Piperidine-2,4-dione 97%;2,4-PIPERADINEDIONE;PIPERIDIN-2,4-DIONE;dihydropyridine-4,6-dione;2,4-Dioxopiperidine;2,4-Piperidinedione, 95+% | | CAS: | 50607-30-2 | | MF: | C5H7NO2 | | MW: | 113.11 | | EINECS: | 803-771-9 | | Product Categories: | Pharmaceutical intermediate;Heterocycles series | | Mol File: | 50607-30-2.mol |  |
| | 2,4-Piperadinedione Chemical Properties |
| Melting point | 98.0 to 102.0 °C | | Boiling point | 362.1±35.0 °C(Predicted) | | density | 1.184±0.06 g/cm3(Predicted) | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | form | powder to crystal | | pka | 12.00±0.70(Predicted) | | color | White to Orange to Green | | InChI | InChI=1S/C5H7NO2/c7-4-1-2-6-5(8)3-4/h1-3H2,(H,6,8) | | InChIKey | RDNZDMDLRIQQAX-UHFFFAOYSA-N | | SMILES | N1CCC(=O)CC1=O |
| Hazard Codes | Xn | | Risk Statements | 22-36/37/38-43 | | Safety Statements | 26-36/37 | | RIDADR | UN 3335 | | WGK Germany | 3 | | HS Code | 2933790090 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
Skin Sens. 1
STOT SE 3 |
| | 2,4-Piperadinedione Usage And Synthesis |
| Description | 2,4-Piperidinedione is an important piperidine ring-containing intermediate, and its 2,4-piperidinedione, as a characteristic fragment, is widely used as an intermediate in the synthesis of ibrutinib and paliperidone drugs. | | Chemical Properties | White to light yellow solid | | Uses | 2,4-Piperidinedione is a reactant in the synthesis of 1,4-dihydropyridines as TGFβ/Smad inhibitors. | | Preparation | The synthesis of 2,4-Piperidinedione involved dissolving 400 mg (2.34 mmol, 1.00 eq.) of Methyl 2,4-dioxo-piperidine-3-carboxylate in a mixture of acetonitrile (20 mL) and water (0.2 mL). The solution was then heated to approximately 86° C. and maintained at this temperature for around 4 hours. After completion of the reaction, the solvent was removed under vacuum, leaving behind a residue of 2,4-Piperidinedione. This residue was further purified using silica gel column chromatography with a mobile phase consisting of dichloromethane and methanol in a ratio of 100:1. The target product, 2,4-Piperidinedione, was obtained as a white solid, with a yield of 27%, corresponding to 70 mg. | | Synthesis | The general procedure for the synthesis of 2,4-piperidinediones from tert-butyl 2,4-dipiperidone-1-carboxylate was as follows: at 0 °C and under nitrogen protection, Boc-β-alanine (25 g, 132 mmol), Meldrum acid (20.9 g, 145 mmol), and 4-dimethylaminopyridine (DMAP, 24.2 g, 198 mmol) were dissolved in 700 mL of anhydrous dichloromethane (DCM). To this solution was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI, 30.4 g, 158 mmol). The reaction mixture was slowly warmed to room temperature and stirred overnight. After completion of the reaction, the reaction mixture was washed with 5% KHSO4 aqueous solution (0.5 L x 4). The organic layer was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the crude product [tert-butyl [3-(2,2-dimethyl-4,6-dioxo-[1,3]dioxol-5-yl)-3-oxo-propyl]-carbamate. The crude product was dissolved in 600 mL of ethyl acetate and refluxed for 4 hours. It was concentrated under reduced pressure to a volume of about 150 mL and subsequently crystallized at 4°C overnight. The solid was collected by filtration and washed with cold ethyl acetate to afford 18.4 g (65% yield) of 2,4-piperidinedione.1H NMR (400 MHz, DMSO-D6) δppm: 1.44 (s, 9H), 2.44 (m, 2H), 3.71 (m, 2H), 4.95 (s, 1H), 11.2 (bs, 1H). The resulting product was converted quantitatively to piperidine-2,4-dione by dissolving in dichloromethane and treating with trifluoroacetic acid for 3 h at room temperature. | | References | [1] Patent: WO2008/104475, 2008, A1. Location in patent: Page/Page column 22
[2] Patent: WO2012/35078, 2012, A1. Location in patent: Page/Page column 144
[3] Patent: US2014/45872, 2014, A1. Location in patent: Paragraph 0911
[4] Journal of Medicinal Chemistry, 2008, vol. 51, # 3, p. 487 - 501
[5] Angewandte Chemie - International Edition, 2014, vol. 53, # 14, p. 3594 - 3598 |
| | 2,4-Piperadinedione Preparation Products And Raw materials |
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