HCID 22678549, compound → HCID 22678390, compound

HRID 1837735Notes

Reaction equation

HRID 1837735 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][CH:17]([OH:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:12][CH2:11]2)=[CH:7][CH:6]=[CH:5][N:4]=1>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[CH3:1][O:2][C:3]1[C:8]([CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][C:17](=[O:24])[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:12][CH2:11]2)=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

4

Reactant 1

HCID 22678549HCID 22678549, compound

Product 1

HCID 22678390HCID 22678390, compoundYield 70.4%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

2.2 g of 1-[(2-methoxy-3-pyridyl)methyl]-4-(2-hydroxy-2-phenylethyl)piperidine and 8.6 g of manganese dioxide were suspended in 35 ml of toluene, and the mixture was heated under reflux for 2 hours. The reaction solution was filtered, and the filtrate was evaporated. Then, the residue was purified and separated by silica gel column chromatography (ethyl acetate), to give 1.54 g of the title compound as a pale yellow oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. filtrationThe reaction solution was filtered
  4. customthe filtrate was evaporated
  5. customThen, the residue was purified
  6. customseparated by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-7670810869ef425a9358e36784a0f6ee
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

Loading…