Hydrochloric Acid → Benzenemethanamine, 4-bromo-2-fluoro-.alpha.-methyl-, hydrochloride (1:1), (.alpha.R)-

HRID 1404566Notes

Reaction equation

HRID 1404566 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:10][S@](C(C)(C)C)=O)[CH3:9])=[C:4]([F:17])[CH:3]=1.[ClH:18].O1CCOCC1>CO>[ClH:18].[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH2:10])[CH3:9])=[C:4]([F:17])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 16102886HCID 16102886, compound

Product 1

HCID 16102887Benzenemethanamine, 4-bromo-2-fluoro-.alpha.-methyl-, hydrochloride (1:1), (.alpha.R)-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-2-methyl-propane-2-sulfinic acid [(R)-1-(4-bromo-2-fluoro-phenyl)-ethyl]-amide (4.02 g, 12.5 mmol) in methanol (25 ml) was added a 4M HCl solution in dioxane (6.24 ml, 25.0 mmol) and the mixture was stirred for 4 h. The reaction mixture was then concentrated and diethyl ether was added. The resulting suspension was stirred for 2 h and then filtered to deliver the title compound as white solid (3.11 g, 98%).

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. additiondiethyl ether was added
  3. stirringThe resulting suspension was stirred for 2 h
  4. filtrationfiltered

Sources & evidence

ORD record
ord-c4adba9c5cd344a48c00c3e4a5cae258
Source dataset
uspto-grants-2014_12
Patent number
US08912221B2

Reaction notes

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