6-[5-hydroxy-2-(2,2,2-trifluoroethoxy)benzamidomethyl]-2(1H)-pyridone → 5-Hydroxy-N-((6-oxo-2-piperidinyl)methyl)-2-(2,2,2-trifluoroethoxy)benzamide

HRID 2413342Notes

Reaction equation

HRID 2413342 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH2:20][C:21]([F:24])([F:23])[F:22])=[C:6]([CH:18]=1)[C:7]([NH:9][CH2:10][C:11]1[NH:16][C:15](=[O:17])[CH:14]=[CH:13][CH:12]=1)=[O:8]>[Rh].CO>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH2:20][C:21]([F:24])([F:22])[F:23])=[C:6]([CH:18]=1)[C:7]([NH:9][CH2:10][CH:11]1[CH2:12][CH2:13][CH2:14][C:15](=[O:17])[NH:16]1)=[O:8]

Participants

4

Reactant 1

HCID 135635926-[5-hydroxy-2-(2,2,2-trifluoroethoxy)benzamidomethyl]-2(1H)-pyridone

Product 1

HCID 104727845-Hydroxy-N-((6-oxo-2-piperidinyl)methyl)-2-(2,2,2-trifluoroethoxy)benzamide

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 0.16 g (0.468 mmole) of 6-[5-hydroxy-2-(2,2,2-trifluoroethoxy)benzamidomethyl]-2(1H)-pyridone, 0.05 g of 5% rhodium on alumina and 50 ml of methanol was hydrogenated on a Parr apparatus for 50 minutes. The mixture was filtered, the filtrate was evaporated, and the residue was dried to provide 5-hydroxy-N-(6-oxo-2-piperidylmethyl)-2-(2,2,2-trifluoroethoxy)benzamide.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated
  3. customthe residue was dried

Sources & evidence

ORD record
ord-50fb9ce503334eb0a2739a3abf8d02fe
Source dataset
uspto-grants-1985_01
Patent number
US04496734

Reaction notes

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