Ammonia → 4,5,6,7-Tetrahydrothieno[2,3-c]pyridin-4-ol

HRID 1511596

Reaction equation

HRID 1511596 reaction equation
C([O:3][CH:4](OCC)[CH2:5][NH:6][CH2:7][C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)C.N>Cl>[S:9]1[C:8]2[CH2:7][NH:6][CH2:5][CH:4]([OH:3])[C:12]=2[CH:11]=[CH:10]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 27953962,2-diethoxy-N-(thiophen-2-ylmethyl)ethanamine

Product 1

HCID 123370234,5,6,7-Tetrahydrothieno[2,3-c]pyridin-4-olYield 28.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

2,2-Diethoxy-N-(thiophen-2-ylmethyl)ethaneamine (72.5 g) prepared in the step 2 was dissolved in 5N aqueous solution of hydrochloric acid and stirred overnight at room temperature. The reaction solution was neutralized with 10% aqueous ammonia and subjected to extraction with ethyl acetate. The organic layer was separated, washed with water and a saturated solution of sodium chloride successively, dried over anhydrous magnesium sulfate and the solvent was evaporated therefrom in vacuo. The residue was purified by silica gel column chromatography to give 14.0 g of the objective compound.

Workup

  1. extractionsubjected to extraction with ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materiala saturated solution of sodium chloride successively, dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-08eb0dac5f7d41f381ee68cbddfad073
Source dataset
uspto-grants-2012_07
Patent number
US08217031B2

Linked notes

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