2,4-Dioxo-[1,1']bipiperidinyl-3-carboxylic acid methyl ester → [1,1']Bipiperidinyl-2,4-dione

HRID 2102870Notes

Reaction equation

HRID 2102870 reaction equation
COC([CH:5]1[C:10](=[O:11])[CH2:9][CH2:8][N:7]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[C:6]1=[O:18])=O>C(O)(=O)C>[N:7]1([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH2:8][CH2:9][C:10](=[O:11])[CH2:5][C:6]1=[O:18]

Participants

3

Reactant 1

HCID 578035922,4-Dioxo-[1,1']bipiperidinyl-3-carboxylic acid methyl ester

Product 1

HCID 22038474[1,1']Bipiperidinyl-2,4-dioneYield 36%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The ethyl ester product from step 3 was dissolved in 10% acetic acid (250 ml) and the solution boiled under reflux for one hour. The cooled reaction mixture was evaporated, and the residue purified by flash chromatography (CH2Cl2: acetone 9:1-1:1) to give 4.00 g (36%) of the title compound as a semi-solid.

Workup

  1. temperatureunder reflux for one hour
  2. customThe cooled reaction mixture
  3. customwas evaporated
  4. customthe residue purified by flash chromatography (CH2Cl2: acetone 9:1-1:1)

Sources & evidence

ORD record
ord-dcdbc33c477a4406acb0f1dacd8896ca
Source dataset
uspto-grants-2009_08
Patent number
US07576095B2

Reaction notes

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