Hydrochloric Acid → (r)-1-(5-Bromo-pyridin-2-yl)-ethylamine dihydrochloride

HRID 2038782Notes

Reaction equation

HRID 2038782 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]([NH:10][S@@](C(C)(C)C)=O)[CH3:9])=[N:6][CH:7]=1.[ClH:17].CCOCC>CO>[ClH:17].[ClH:17].[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]([NH2:10])[CH3:9])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 68237516(R)-2-methyl-propane-2-sulfinic acid[(R)-1-(5-bromo-pyridin-2-yl)-ethyl]-amide

Product 1

HCID 68378980(r)-1-(5-Bromo-pyridin-2-yl)-ethylamine dihydrochlorideYield 101%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (R)-2-methyl-propane-2-sulfinic acid[(R)-1-(5-bromo-pyridin-2-yl)-ethyl]-amide (500 mg, 1.64 mmol) in 5 mL of MeOH was added HCl (4.10 mL, 16.4 mmol, 4M in dioxane). The reaction mixture was stirred at room temperature for 2.5 h, during which time a white precipitate was formed. 20 mL of Et2O was added. After stirring for an additional 20 min, the reaction mixture was filtered, washing with 10 mL of Et2O. 454 mg (99%) of the title compound was isolated as a white solid after drying under high vacuum.

Workup

  1. customwas formed
  2. stirringAfter stirring for an additional 20 min
  3. filtrationthe reaction mixture was filtered
  4. washwashing with 10 mL of Et2O

Sources & evidence

ORD record
ord-f4935b4666d0494eb6d8ebe19039638f
Source dataset
uspto-grants-2013_11
Patent number
US08575360B2

Reaction notes

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