HCID 23081427, compound → HCID 6623740, compound

HRID 856071Notes

Reaction equation

HRID 856071 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[NH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:16]=[CH:17][C:18]([O:21][C:22]([F:23])([F:24])[F:25])=[CH:19][CH:20]=2)[CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 23081427HCID 23081427, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 6623740HCID 6623740, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of (1-benzylpiperidin-4-yl)-(4-trifluoromethoxyphenyl)amine (3.0 g, 8.3 mmol) prepared in Reference Example 129 and a catalytic amount of 10% palladium/carbon in ethanol (30 ml) was refluxed under an atmospheric pressure of hydrogen for 20 hours. The reaction mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/methanol=10/1) to afford piperidin-4-yl-(4-trifluoromethoxyphenyl)amine (2.02 g, yield 94%) as a colorless crystalline powder.

Workup

  1. customprepared in Reference Example 129
  2. filtrationThe reaction mixture was filtered through Celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (methylene chloride/methanol=10/1)

Sources & evidence

ORD record
ord-f8bc61d24b384ee0be338469491ce01e
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

Loading…