HCID 9922919, compound → HCID 69862217, compound

HRID 395912Notes

Reaction equation

HRID 395912 reaction equation
[ClH:1].C([N:9]1[CH2:14][CH2:13][CH:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11](=[O:22])[CH2:10]1)C1C=CC=CC=1>[Pd].O>[ClH:1].[CH2:15]([CH:12]1[CH2:13][CH2:14][NH:9][CH2:10][C:11]1=[O:22])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 1

HCID 9922919HCID 9922919, compound

Product 1

HCID 69862217HCID 69862217, compoundYield 84.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A suspension consisting of 50.0 g of rac-1,4-dibenzyl-3-oxo-piperidine hydrochloride (0.158 mol), 0.50 l of water and 10.0 g of 5% palladium on charcoal (Pd/C) was stirred under a hydrogen atmosphere until 3.5 l of gas had been consumed (1 h). Then the Pd/C was filtered off and rinsed with water, the filtrate was evaporated and the residue taken up in isopropanol. The crystallization started spontaneously and was completed at 5° C. over night. The precipitate was filtered off, the filter cake was rinsed with cold isopropanol and dried to constant weight (0.2 mbar, room temperature, 2 h) to afford 30 g of rac-4-benzyl-pyperidine-3-one hydrochloride as light yellow crystals. Elemental analysis:

Workup

  1. customhad been consumed (1 h)
  2. filtrationThen the Pd/C was filtered off
  3. washrinsed with water
  4. customthe filtrate was evaporated
  5. customThe crystallization
  6. waitwas completed at 5° C. over night
  7. filtrationThe precipitate was filtered off
  8. washthe filter cake was rinsed with cold isopropanol
  9. customdried to constant weight (0.2 mbar, room temperature, 2 h)

Sources & evidence

ORD record
ord-b23cb3f3f14f4f0abf003a2aac5f6ffe
Source dataset
uspto-grants-2003_08
Patent number
US06605723B2

Reaction notes

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