HCID 18176648, compound → HCID 18176641, compound

HRID 394487Notes

Reaction equation

HRID 394487 reaction equation
Cl.[CH3:2][N:3]([CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=1)CC1C=CC=CC=1.[H][H]>CO.[Pd]>[CH3:2][NH:3][CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:23])([F:24])[F:25])[CH:17]=1

Participants

5

Reactant 2

HCID 18176648HCID 18176648, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18176641HCID 18176641, compoundYield 25.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of intermediate 8 (0.019 mol) in methanol (150 ml) was hydrogenated with palladium on carbon (10%, 2 g) as a catalyst. After uptake of hydrogen gas (1 equivalent), the catalyst was filtered off and the filtrate was evaporated. The residue was converted into the free base with a NaOH solution. The aqueous solution was extracted with toluene. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was converted into the hydrochloric acid salt (1:1) in DIPE. The precipitate was filtered off and dried, yielding 1.21 g (22.5%) of N-methyl-4-[3-(trifluoromethyl)phenoxy]-1-butanamine (intermediate 9).

Workup

  1. customthe filtrate was evaporated
  2. extractionThe aqueous solution was extracted with toluene
  3. customThe organic layer was separated
  4. customdried
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. filtrationThe precipitate was filtered off
  8. customdried

Sources & evidence

ORD record
ord-a07c93163521414481ee3305eddb5b08
Source dataset
uspto-grants-2003_08
Patent number
US06602873B2

Reaction notes

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