Hydrochloric Acid → HCID 90414498, compound

HRID 57463Notes

Reaction equation

HRID 57463 reaction equation
[F:1][C:2]([C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]([NH:13]S(C(C)(C)C)=O)[CH3:12])=[C:7]([F:20])[CH:6]=1)([F:4])[CH3:3].Cl.C(OCC)C>O1CCOCC1>[F:1][C:2]([C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]([NH2:13])[CH3:12])=[C:7]([F:20])[CH:6]=1)([F:4])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 90414411N-((S)-1-(4-(1,1-difluoroethyl)-2-fluorophenyl)ethyl)-2-methylpropane-2-sulfinamide

Product 1

HCID 90414498HCID 90414498, compoundYield 105.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
-10 °C

Procedure

To N—((S)-1-(4-(1,1-difluoroethyl)-2-fluorophenyl)ethyl)-2-methylpropane-2-sulfinamide (349 mg, 1.135 mmol) was added 4M HCl in dioxane (3.01 mL) to give a purple solution. To the mixture was added diethylether (20 mL) and the mixture was stirred for 15 min at −10° C. The mixture was concentrated under reduced pressure to ˜2 mL of volume and diethylether (20 mL) was added. The solids were filtered off, rinsed with diethylether (4×10 mL) and dried under reduced pressure providing (S)-1-(4-(1,1-difluoroethyl)-2-fluorophenyl)ethanamine (244 mg) as an off-white solid (HCl salt). LCMS m/z 204.1 (M+H)+, Rt 0.42 min.

Workup

  1. customto give a purple solution
  2. concentrationThe mixture was concentrated under reduced pressure to ˜2 mL of volume and diethylether (20 mL)
  3. additionwas added
  4. filtrationThe solids were filtered off
  5. washrinsed with diethylether (4×10 mL)
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-bb228b7cb2aa42d1b422db61874dc758
Source dataset
uspto-grants-2016_09
Patent number
US09434719B2

Reaction notes

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