Water → HCID 15453627, compound

HRID 1106487Notes

Reaction equation

HRID 1106487 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][C:7]1(C(OC)=O)[C:12](=[O:13])[CH2:11][CH2:10][N:9]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:8]1)=[O:5])[CH3:2].[Cl-].[Li+].O>CN(C)C=O>[O:13]=[C:12]1[CH2:11][CH2:10][N:9]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:8][CH:7]1[CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 433294Lithium ChlorideHCID 15453626HCID 15453626, compound

Product 1

HCID 15453627HCID 15453627, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 3-ethoxycarbonylmethyl-3-methoxycarbonyl-4-oxo-1-piperidineacetate (1.0 g) and 140 mg of lithium chloride were dissolved in 10 ml of N,N-dimethylformamide and the solution was refluxed for 48 hours. Then, 10 ml of water was added to the reaction liquid, and the mixture was extracted with 100 ml of ethyl acetate. The resulting extract was dried over sodium sulfate and concentrated. The resulting residue was purified by silica gel column chromatography (eluent: chloroform) to give 400 mg of diethyl 4-oxo-1,3-piperidinediacetate as an oily substance.

Workup

  1. temperaturethe solution was refluxed for 48 hours
  2. extractionthe mixture was extracted with 100 ml of ethyl acetate
  3. extractionThe resulting extract
  4. dry with materialwas dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe resulting residue was purified by silica gel column chromatography (eluent: chloroform)

Sources & evidence

ORD record
ord-d6bad635ee7042a5b66689b962b1b55f
Source dataset
uspto-grants-2000_05
Patent number
US06057324

Reaction notes

Loading…