Hydrochloric Acid → (S)-1-(4-Fluorophenyl)-ethylamine

HRID 989806Notes

Reaction equation

HRID 989806 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]([C@@H:6]([N:8]=[N+]=[N-])[CH3:7])=[CH:4][CH:3]=1.Cl>[Pd]>[F:1][C:2]1[CH:12]=[CH:11][C:5]([C@@H:6]([NH2:8])[CH3:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 12050153HCID 12050153, compound

Product 1

HCID 2779063(S)-1-(4-Fluorophenyl)-ethylamineYield 108.3%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of the crude product of Step 2 (1.2 g, 7.3 mmol), conc. HCl (1 ml in 50 ml CH3OH) and Pd/C (10% w/w) (140 mg) was hydrogenated at 60 psi for 4 hr. After removal of the solvent, the residue was redissolved in 20 ml water and washed with ether. The aqueous layer was then basified to pH 11 and extracted with ether. The ether solution was dried and solvent evaporated to give 1.1 gram of (S)-p-fluoro-α-methylbenzylamine.

Workup

  1. customAfter removal of the solvent
  2. dissolutionthe residue was redissolved in 20 ml water
  3. washwashed with ether
  4. extractionextracted with ether
  5. dry with materialThe ether solution was dried
  6. customsolvent evaporated

Sources & evidence

ORD record
ord-df989da00c0a4163a22ea9d22808ada8
Source dataset
uspto-grants-2002_10
Patent number
US06458812B1

Reaction notes

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