Hydrochloric Acid → (R)-1-(4-Chloro-3,5-dimethyl-phenyl)-2-methyl-propylamine hydrochloride

HRID 1629752Notes

Reaction equation

HRID 1629752 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C@H:9]([NH:13][S@@](C(C)(C)C)=O)[CH:10]([CH3:12])[CH3:11])=[CH:4][C:3]=1[CH3:20].Cl>CO>[ClH:1].[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C@H:9]([NH2:13])[CH:10]([CH3:11])[CH3:12])=[CH:4][C:3]=1[CH3:20]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67329434(R)-2-Methyl-propane-2-sulfinic acid [(R)-1-(4-chloro-3,5-dimethyl-phenyl)-2-methyl-propyl]-amide

Product 1

HCID 67346920(R)-1-(4-Chloro-3,5-dimethyl-phenyl)-2-methyl-propylamine hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of intermediate INT 61 (4.53 g, 14.34 mmol) in MeOH (75 mL) was treated with HCl (4 M in dioxane, 7.17 mL, 28.7 mmol) and stirred overnight. After evaporation of the solvents, a solid was obtained which was washed with Et2O. The solid was then dissolved in 10% sodium carbonate solution and extracted twice with EtOAc. The combined organic layers were dried over sodium sulfate, filtered and concentrated. The crude amine was dissolved in Et2O and treated with an excess of an ethereal solution of HCl (2 M). The suspension was concentrated to yield the title compound.

Workup

  1. customAfter evaporation of the solvents
  2. customa solid was obtained which
  3. washwas washed with Et2O
  4. dissolutionThe solid was then dissolved in 10% sodium carbonate solution
  5. extractionextracted twice with EtOAc
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. dissolutionThe crude amine was dissolved in Et2O
  10. additiontreated with an excess of an ethereal solution of HCl (2 M)
  11. concentrationThe suspension was concentrated

Sources & evidence

ORD record
ord-ffa3c1a60551467f95be3d262370ab3d
Source dataset
uspto-grants-2014_07
Patent number
US08791100B2

Reaction notes

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