HCID 178524453, compound → HCID 178524454, compound

HRID 990212Notes

Reaction equation

HRID 990212 reaction equation
[CH2:1]([N:8]=[C:9]([C:11]1[C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=[CH:13][N:12]=1)[OH:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1(C)C=CC=CC=1.[Pd]>[CH2:1]([N:8]=[C:9]([CH:11]1[CH:16]([C:17]([OH:19])=[O:18])[CH2:15][CH2:14][CH2:13][NH:12]1)[OH:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 178524453HCID 178524453, compound

Product 1

HCID 178524454HCID 178524454, compoundYield 90.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

In a 1.3 liter stirred autoclave fitted with stirrer, temperature sensor, and riser tube, 666 g of pyridine-2,3-dicarboxylic acid N-benzylimide and 28.2 g of 5% by weight palladium-on-carbon were suspended in 959 g of toluene. The autoclave was then flushed, hydrogen was introduced, and the autoclave was heated at a reaction temperature of 80° C. as described in Example 1. Work-up of the reaction mixture as described in Example 1 gave 618 g of piperidine-2,3-dicarboxylic acid N-benzylimide in a purity of 98.7% (GC area percent).

Workup

  1. customfitted with stirrer
  2. customThe autoclave was then flushed
  3. additionhydrogen was introduced

Sources & evidence

ORD record
ord-98fe8e2be176458d8548d17745901f5b
Source dataset
uspto-grants-2002_10
Patent number
US06458954B2

Reaction notes

Loading…