HCID 59509446, compound → Diethyl piperidine-4,4-dicarboxylate

HRID 2407481Notes

Reaction equation

HRID 2407481 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:11][CH2:10][N:9](CC2C=CC=CC=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[H][H]>C(O)C.[Pd]>[CH2:1]([O:3][C:4]([C:6]1([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 59509446HCID 59509446, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18930984Diethyl piperidine-4,4-dicarboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of benzylpiperidine-4,4-dicarboxylic acid diethyl ester (21.5 g, 0.067 mol) in ethanol (300 mL) is added 5% Pd/C (25 g, 50% wet). The reaction mixture is stirred under 40 psi pressure of hydrogen for 3 hrs, then filtered through a celite bed and the filtrate is concentrated to give a crude viscous liquid which is purified by column chromatography (silica gel 230-400 mesh, methanol:dichloromethane 10:90) to furnish piperidine-4,4-dicarboxylic acid diethyl ester as pale yellow liquid.

Workup

  1. filtrationfiltered through a celite bed
  2. concentrationthe filtrate is concentrated
  3. customto give a crude viscous liquid which
  4. customis purified by column chromatography (silica gel 230-400 mesh, methanol:dichloromethane 10:90)

Sources & evidence

ORD record
ord-d43e2338c45a4849b400e58de58c56bd
Source dataset
uspto-grants-2014_08
Patent number
US08809539B2

Reaction notes

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