ChemicalBook CAS DataBase List 2,4-Piperadinedione

2,4-Piperadinedione synthesis

5synthesis methods

Product Name:2,4-Piperadinedione
CAS Number:50607-30-2
Molecular formula:C5H7NO2
Molecular Weight:113.11

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.

TERT-BUTYL 2,4-DIOXOPIPERIDINE-1-CARBOXYLATE

845267-78-9
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$10.00/1g

50607-30-2
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$13.00/250mg

Yield:50607-30-2 100%

Reaction Conditions:

with trifluoroacetic acid in dichloromethane at 20; for 3 h;Product distribution / selectivity;

Steps:

1
Boc-β-alanine (25 g, 132 mmol), Meldrum's acid (20.9 g, 145 mmol) and 4- dimethylaminopyridine (DMAP, 24.2 g, 198 mmol) were dissolved in 700 mL of dry dichloromethane (DCM) at 0⁰C under nitrogen atmosphere. To this solution 1-(3- dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI, 30.4 g, 158 mmol) was added. The resulting solution was allowed to reach room temperature and stirred overnight. The reaction mixture was washed (0.5 L x 4) with 5% KHSO₄ aqueous solution. The organic layer was dried over anh. Na₂SO₄, filtered and evaporated under vacuum, affording crude [3-(2,2-dimethyl-4,6-dioxo-[1 ,3]dioxan-5-yl)-3-oxo-propyl]- carbamic acid tert-butyl ester that was dissolved in 600 mL of ethylacetate and refluxed for 4 hours. The solvent was reduced to 150 mL under vacuum and the resulting solution was allowed to crystallize at 4°C overnight. The solid was filtered and washed with cold ethyl acetate affording 18.4 g (65% yield) of the title compound.1 H NMR (400 MHz, DMSO-D6) δ ppm 1.44 (s, 9 H) 2.44 (m, 2 H) 3.71 (m, 2 H) 4.95 (s,1 H) 11.2 (bs, 1 H). The compound thus obtained can be converted into piperidine-2,4-dione in quantitative yield by dissolving it in dichloromethane and treating with trifluoroacetic acid at room temperature for 3 hours.

References:

NERVIANO MEDICAL SCIENCES S.R.L. WO2008/104475, 2008, A1 Location in patent:Page/Page column 22

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