Sodium → 1-Methyl-2,4-piperidinedione

HRID 887486Notes

Reaction equation

[Na].C(OC(=O)[CH2:6][CH2:7][N:8]([CH3:17])[C:9](=[O:16])[CH2:10][C:11]([O:13]CC)=O)C.CN1CCC(=O)C(C(OCC)=O)C1=O>C(O)C.CCOCC>[CH3:17][N:8]1[CH2:7][CH2:6][C:11](=[O:13])[CH2:10][C:9]1=[O:16]

Participants

Conditions

Temperature: 80 °C

Procedure

Into a 50-mL round bottomed flask was added ethanol (4 mL) under argon, followed by sodium (0.121 g, 5.25 mmol). The mixture was stirred at room temperature for 15 min, during which a solution of ethyl 3-((3-ethoxy-3-oxopropyl)(methyl)amino)-3-oxopropanoate (1.17 g, 4.77 mmol) in ethanol (5 mL) was added. The resulting clear, colorless mixture was heated at 80° C. for 1 h, during which LC-MS indicated completion of reaction and a clean conversion to the desired ethyl 1-methyl-2,4-dioxopiperidine-3-carboxylate intermediate. Upon cooling to room temperature, the reaction was diluted with Et2O, resulting in the formation of a white precipitate (desired product). The white precipitate was collected via filtration, taken up in 5% aqueous HCl solution (8 mL), and refluxed for 1 h. The cooled mixture was extracted with CH2Cl2 (5×) and the combined organic extracts were dried (MgSO4), filtered, and concentrated in vacuo. Flash column chromatography (20% EtOAc/Hexanes to 100% EtOAc) afforded 1-methylpiperidine-2,4-dione as a viscous milky oil. [M+1]=128.1.

Workup

additionwas added
customcompletion of reaction
temperatureUpon cooling to room temperature

Sources & evidence

ORD record: ord-7db5501816e3421db1d1e4ba27d8a59f
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247418B2

Reaction notes

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