p-Toluenesulfonic acid → 3-Fluoro-5-trifluoromethylphenethylamine Tosylate

HRID 844323Notes

Reaction equation

HRID 844323 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:12][C:13]#[N:14])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21]([OH:24])(=[O:23])=[O:22])=[CH:17][CH:16]=1>COCCO.[Pd]>[S:21]([C:18]1[CH:19]=[CH:20][C:15]([CH3:25])=[CH:16][CH:17]=1)([OH:24])(=[O:23])=[O:22].[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:7]=1)[CH2:12][CH2:13][NH2:14]

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 27376013-Fluoro-5-(trifluoromethyl)phenylacetonitrile

Product 1

HCID 865839643-Fluoro-5-trifluoromethylphenethylamine Tosylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 80192-MethoxyethanolSolvent

Procedure

A solution of 2.5 g of 3-fluoro-5-trifluoromethylphenylacetonitrile and 2.34 g (12.3 mmol) of p-toluenesulfonic acid in 75 ml of ethylene glycol monomethyl ether is hydrogenated for 3 hours at room temperature at 40 psi, using 200 mg 10% palladium on carbon catalyst. The catalyst is filtered off and the solvent evaporated to half the volume. Upon standing, the p-toluenesulfonic acid salt of the desired 3-fluoro-5-trifluoromethylphenethylamine crystallizes. The white crystals, 4.26 g (91%) are collected by filtration.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe solvent evaporated to half the volume
  3. customthe p-toluenesulfonic acid salt of the desired 3-fluoro-5-trifluoromethylphenethylamine crystallizes
  4. filtrationThe white crystals, 4.26 g (91%) are collected by filtration

Sources & evidence

ORD record
ord-e38ce15c584744f3a4641c36ab567390
Source dataset
uspto-grants-2002_04
Patent number
US06380243B1

Reaction notes

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