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

HRID 1629733Notes

Reaction equation

HRID 1629733 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C@H:9]([NH:12][S@@](C(C)(C)C)=O)[CH2:10][CH3:11])=[CH:4][C:3]=1[CH3:19].Cl>CO>[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C@H:9]([NH2:12])[CH2:10][CH3:11])=[CH:4][C:3]=1[CH3:19]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67346503(R)-2-Methyl-propane-2-sulfinic acid [(R)-1-(4-chloro-3,5-dimethyl-phenyl)-propyl]-amide

Product 1

HCID 55278509(R)-1-(4-Chloro-3,5-dimethyl-phenyl)-propylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of intermediate INT 37 (3.4 g, 11.26 mmol) in MeOH (75 mL) was treated with HCl (4 M in dioxane, 5.63 mL, 22.53 mmol) and stirred overnight. After evaporation of the solvents, a white solid was obtained which was washed with Et2O. The solid was then dissolved in water, slightly acidified with 2 M HCl and washed with EtOAc. The aqueous layer was separated and the pH adjusted to about 11 using 2 M NaOH followed by extraction with Et2O (3×). The Et2O layers were combined, dried over sodium sulfate, filtered and concentrated.

Workup

  1. customAfter evaporation of the solvents
  2. customa white solid was obtained which
  3. washwas washed with Et2O
  4. dissolutionThe solid was then dissolved in water
  5. washwashed with EtOAc
  6. customThe aqueous layer was separated
  7. extractionfollowed by extraction with Et2O (3×)
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-ae478501eebb4f68a7ff21c73d12850d
Source dataset
uspto-grants-2014_07
Patent number
US08791100B2

Reaction notes

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