Ethyl 2,4-dioxo-1-(piperidin-1-yl)piperidine-3-carboxylate → [1,1']Bipiperidinyl-2,4-dione

HRID 1790039Notes

Reaction equation

HRID 1790039 reaction equation
[O:1]=[C:2]1[CH:7](C(OCC)=O)[C:6](=[O:13])[CH2:5][CH2:4][N:3]1[N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>CC(O)=O>[N:3]1([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH2:4][CH2:5][C:6](=[O:13])[CH2:7][C:2]1=[O:1]

Participants

3

Reactant 1

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

Product 1

HCID 22038474[1,1']Bipiperidinyl-2,4-dioneYield 22%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
125 °C

Procedure

Ethyl 2,4-dioxo-1,1′-bipiperidine-3-carboxylate (11.36 g, 42.38 mmol, Example 14) was dissolved in 10% AcOH (200 mL) and heated at reflux 125° C. for 1 h. The cooled reaction was evaporated, and the residue was purified by flash chromatography using a gradient of 9:1 to 1:1 CH2Cl2/acetone, to give the product as a yellow viscous oil (6.4 g, 22% yield for the two last steps).

Workup

  1. temperatureheated
  2. customThe cooled reaction
  3. customwas evaporated
  4. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-68ade4b66e4b4b659a2a112d0fd74d5d
Source dataset
uspto-grants-2006_07
Patent number
US07071207B2

Reaction notes

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