HCID 799039, compound → HCID 19082933, compound

HRID 1901815Notes

Reaction equation

HRID 1901815 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:8][C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:2]=1.[H][H]>C(O)C.Cl.[Pd]>[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH2:7][NH:8][C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:2]1

Participants

6

Reactant 2

HCID 799039HCID 799039, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19082933HCID 19082933, compoundYield 82.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

Ba) A solution of 42.5 g of N-(3-pyridinylmethyl)-benzamide in 220 ml of ethanol and 220 ml of 1N hydrochloric acid is treated with 4.2 g of palladium on charcoal and hydrogenated at room temperature for 24 hours over 100 bar of hydrogen. Then, the catalyst is filtered off and the filtrate is evaporated. The residue is taken up in methylene chloride and shaken with 1N sodium hydroxide solution. The organic phase is washed with water, dried and evaporated. There are obtained 36.1 g of (RS)-N-piperidin-3-ylmethyl-benzamide, MS (FAB): 218M+.

Workup

  1. filtrationThen, the catalyst is filtered off
  2. customthe filtrate is evaporated
  3. washThe organic phase is washed with water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-e0dc1dfc03c544bd87c8990d8f3a298f
Source dataset
uspto-grants-1996_11
Patent number
US05578594

Reaction notes

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