Cesium carbonate → Ethyl 2,4-dioxo-1-(piperidin-1-yl)piperidine-3-carboxylate

HRID 1790038Notes

Reaction equation

HRID 1790038 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][C:6]([N:8]([N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[CH2:9][CH2:10][C:11]([O:13]C)=O)=[O:7])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1.CN(C=O)C>[O:7]=[C:6]1[CH:5]([C:4]([O:3][CH2:1][CH3:2])=[O:21])[C:11](=[O:13])[CH2:10][CH2:9][N:8]1[N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 2

HCID 10796Cesium carbonateHCID 22038467methyl N-(3-ethoxy-3-oxopropanoyl)-N-(1-piperidinyl)-beta-alaninate

Product 1

HCID 22038502Ethyl 2,4-dioxo-1-(piperidin-1-yl)piperidine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
77 °C

Procedure

To a solution of methyl N-(3-ethoxy-3-oxopropanoyl)-N-(1-piperidinyl)-β-alaninate (43 g, 143 mmol) in a mixture of THF (2.26 L) and DMF (1.00 L) was added Cs2CO3 (140 g, 430 mmol). The resulting mixture was heated at reflux (77° C.) for 48 h. The cooled reaction was filtered, and the filtrate was evaporated. The filtrate residue and filtered solid were combined and purified by flash chromatography using 7:3 CH2Cl2/MeOH as eluant, to give 11.36 g of partially pure title material. LC-MS m/z 269.19 (MH+), retention time 2.20 min (method 2).

Workup

  1. temperatureThe resulting mixture was heated
  2. customThe cooled reaction
  3. filtrationwas filtered
  4. customthe filtrate was evaporated
  5. filtrationThe filtrate residue and filtered solid
  6. custompurified by flash chromatography
  7. customto give 11.36 g of partially pure title material

Sources & evidence

ORD record
ord-a7f3b81c55c44181a9904755fcdbcc78
Source dataset
uspto-grants-2006_07
Patent number
US07071207B2

Reaction notes

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