Hydrochloric Acid → (S)-1-(4-Bromo-2-methyl-phenyl)-ethylamine

HRID 1191883Notes

Reaction equation

HRID 1191883 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([NH:11][S@@](C(C)(C)C)=O)[CH3:10])=[C:5]([CH3:18])[CH:4]=1>C(OCC)(=O)C>[Br:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([NH2:11])[CH3:10])=[C:5]([CH3:18])[CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58102376(R)-2-methyl-propane-2-sulfinic acid [(S)-1-(4-bromo-2-methyl-phenyl)-ethyl]amide

Product 1

HCID 58102386(S)-1-(4-Bromo-2-methyl-phenyl)-ethylamine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Hydrochloric acid (4 mol/L in 1,4-dioxane, 46 mL) was added to a solution of (R)-2-methyl-propane-2-sulfinic acid [(S)-1-(4-bromo-2-methyl-phenyl)-ethyl]-amide (crude from Step 2, 8.85 g, ca. 75% pure) in ethyl acetate (80 mL) at room temperature. The solution was stirred at room temperature for 1 h and then concentrated. The residue was taken up in water and the resulting mixture was washed with diethyl ether. The aqueous phase was basified using aqueous 1 M NaOH solution and extracted with dichloromethane. The combined extracts were washed with brine, dried (MgSO4), and concentrated to afford the title compound. Yield: 4.04 g (905 of theory); Mass spectrum (ESI−): m/z=214/216 (Br) [M+H]+.

Workup

  1. concentrationconcentrated
  2. washthe resulting mixture was washed with diethyl ether
  3. extractionextracted with dichloromethane
  4. washThe combined extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4931f1db391c4c72a1196dd6edd2da93
Source dataset
uspto-grants-2014_03
Patent number
US08680093B2

Reaction notes

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