Hydrochloric Acid → (R)-1-(6-bromo-pyridin-3-yl)-ethylamine HCl salt

HRID 2038751Notes

Reaction equation

HRID 2038751 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([C@H:8]([NH:10]S(C(C)(C)C)=O)[CH3:9])=[CH:4][CH:3]=1.[ClH:17].O1CCOCC1.CCOCC>CO>[ClH:17].[Br:1][C:2]1[N:7]=[CH:6][C:5]([C@H:8]([NH2:10])[CH3:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 312751,4-DioxaneHCID 889592202-methyl-propane-2-sulfinic acid[(R)-1-(6-bromo-pyridin-3-yl)-ethyl]-amide

Product 1

HCID 53487712(R)-1-(6-bromo-pyridin-3-yl)-ethylamine HCl saltYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-methyl-propane-2-sulfinic acid[(R)-1-(6-bromo-pyridin-3-yl)-ethyl]-amide (650 mg, 2.13 mmol) in MeOH (5 mL) was added 4.0M HCl in dioxane (5.32 mL, 21.30 mmol). The clear reaction mixture was stirred at room temperature for 2.5 h. The reaction mixture became cloudy during this time. Ether (20 mL) was added, and the mixture was stirred for 10 min and then filtered, washed with ether (20 mL) to afford (R)-1-(6-bromo-pyridin-3-yl)-ethylamine HCl salt (500 mg, 87%) as a white solid.

Workup

  1. stirringthe mixture was stirred for 10 min
  2. filtrationfiltered
  3. washwashed with ether (20 mL)

Sources & evidence

ORD record
ord-65baaa4f989049aaa2c3e6e1cb9a0a31
Source dataset
uspto-grants-2013_11
Patent number
US08575360B2

Reaction notes

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