Potassium Carbonate → 4-Hydroxy-6-mesyl-4,5,6,7-tetrahydro thieno[2,3-c]pyridine

HRID 2413129Notes

Reaction equation

HRID 2413129 reaction equation
Cl.[OH:2][CH:3]1[CH2:8][NH:7][CH2:6][C:5]2[S:9][CH:10]=[CH:11][C:4]1=2.C(=O)([O-])[O-].[K+].[K+].[CH3:18][S:19](Cl)(=[O:21])=[O:20]>C(Cl)(Cl)Cl>[OH:2][CH:3]1[CH2:8][N:7]([S:19]([CH3:18])(=[O:21])=[O:20])[CH2:6][C:5]2[S:9][CH:10]=[CH:11][C:4]1=2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 123370244,5,6,7-Tetrahydrothieno[2,3-c]pyridin-4-ol;hydrochloride

Product 1

HCID 543441984-Hydroxy-6-mesyl-4,5,6,7-tetrahydro thieno[2,3-c]pyridineYield 76%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a mixture of 4-hydroxy-4,5,6,7-tetrahydro-thieno-[2,3-c]pyridine hydrochloride (50 g; 0.26 mole), chloroform (200 ml) and saturated aqueous potassium carbonate solution (100 ml) is added dropwise a solution of methanesulfonyl chloride (30 g; 0.26 mole) in chloroform (50 ml), at room temperature and with vigorous mechanical stirring. Stirring is continued a further 2 hours at room temperature. After decantation, the chloroform phase is washed with dilute hydrochloric acid, then with water, and is dried over anhydrous sodium sulfate. Evaporation of the solvent, in vacuo, leaves crystals which are recrystallized from methanol. Light brown crystals; M.p.=140° C. (methanol); Yield: 76%.

Workup

  1. customat room temperature
  2. washAfter decantation, the chloroform phase is washed with dilute hydrochloric acid
  3. dry with materialwith water, and is dried over anhydrous sodium sulfate
  4. customEvaporation of the solvent
  5. customin vacuo, leaves crystals which
  6. customare recrystallized from methanol

Sources & evidence

ORD record
ord-56517607782d415fbf62b84c9158e6f3
Source dataset
uspto-grants-1985_01
Patent number
US04496568

Reaction notes

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