Hydrochloric Acid → 1-(5-Bromo-pyridin-3-yl)-butylamine

HRID 2067958Notes

Reaction equation

HRID 2067958 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([NH:12]S(C(C)(C)C)=O)[CH2:9][CH2:10][CH3:11])[CH:5]=[N:6][CH:7]=1.Cl>>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([NH2:12])[CH2:9][CH2:10][CH3:11])[CH:5]=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 584433932-Methyl-propane-2-sulfinic acid 1-(5-bromo-pyridin-3-yl)-butylamide

Product 1

HCID 584433761-(5-Bromo-pyridin-3-yl)-butylamineYield 86.4%

Procedure

2-Methyl-propane-2-sulfinic acid 1-(5-bromo-pyridin-3-yl)-butylamide (16 g, 48 mmol) is treated with aqueous HCl (3.0 N solution, 400 mL, 1.2 mol) at room temperature and stirred for 5 hours. The reaction mixture is quenched by addition of saturated aqueous sodium carbonate solution until pH 8 and extracted with dichloromethane (3×300 mL). The combined organic phases are dried over Na2SO4, filtered, and concentrated to afford 1-(5-bromo-pyridin-3-yl)-butylamine (9.5 g, 86%) of as a light brown oil.

Workup

  1. customThe reaction mixture is quenched by addition of saturated aqueous sodium carbonate solution until pH 8
  2. extractionextracted with dichloromethane (3×300 mL)
  3. dry with materialThe combined organic phases are dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a537609bc38f44a3875115e7ca624209
Source dataset
uspto-grants-2012_10
Patent number
US08293917B2

Reaction notes

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