Hydrogen Bromide → 4,5,6,7-Tetrahydrothieno(3,2-c)pyridine

HRID 2301108Notes

Reaction equation

HRID 2301108 reaction equation
Cl.[S:2]1[C:10]2[CH2:9][CH2:8][NH:7][CH2:6][C:5]=2[CH:4]=[C:3]1C(O)=O.Br.[OH-].[Na+]>>[S:2]1[C:10]2[CH2:9][CH2:8][NH:7][CH2:6][C:5]=2[CH:4]=[CH:3]1

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 686439894,5,6,7-Tetrahydrothieno[3,2-c]pyridine-2-carboxylic acid hydrochloride

Product 1

HCID 30850764,5,6,7-Tetrahydrothieno(3,2-c)pyridine

Procedure

4,5,6,7-Tetrahydro-thieno[3,2-c]pyridine-2-carboxylic acid hydrochloride (260 mg, 1.2 mmol) was mixed with 47% hydrogen bromide aqueous solution (3 ml) and heated under reflux for 4 hours. The reaction solution was returned to room temperature and alkalified by adding sodium hydroxide aqueous solution (5 N), and the reaction product was extracted with diethyl ether, washed with saturated brine and then dried with anhydrous magnesium sulfate. By evaporating the solvent from the organic layer under a reduced pressure, 160 mg (1.1 mmol, 95% in yield) of the title compound was obtained.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 hours
  3. customwas returned to room temperature
  4. extractionthe reaction product was extracted with diethyl ether
  5. washwashed with saturated brine
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customBy evaporating the solvent from the organic layer

Sources & evidence

ORD record
ord-ef3905e6c0ad4871b5362ba542da70ed
Source dataset
uspto-grants-2002_12
Patent number
US06498251B1

Reaction notes

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