Potassium Carbonate → tert-Butyl 2-((4-methylpiperazin-1-yl)methyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate

HRID 2388727Notes

Reaction equation

HRID 2388727 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.CS(O[CH2:19][C:20]1[S:28][C:27]2[CH2:26][CH2:25][N:24]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:23][C:22]=2[CH:21]=1)(=O)=O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:7][N:8]1[CH2:13][CH2:12][N:11]([CH2:19][C:20]2[S:28][C:27]3[CH2:26][CH2:25][N:24]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:23][C:22]=3[CH:21]=2)[CH2:10][CH2:9]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 86635666tert-Butyl 2-((methylsulfonyloxy)methyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate

Product 1

HCID 57948670tert-Butyl 2-((4-methylpiperazin-1-yl)methyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylateYield 50%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate (26.5 mmol) and N-methylpiperazine (6.36 mmol) was added to a solution of tert-butyl 2-((methylsulfonyloxy)methyl)-6,7-dihydrothieno-[3,2-c]pyridine-5(4H)-carboxylate (5.3 mmol) in toluene (30 ml). The reaction mixture obtained was heated under reflux for 16 hours. The reaction temperature was then reduced to 25° C. and the reaction mixture was diluted with ethyl acetate. The reaction mixture was washed with water and saturated sodium chloride solution and dried over sodium sulfate. After the solvent had been removed under reduced pressure, the crude product obtained was purified by column chromatography (5% methanol in methylene chloride). The desired product was obtained in a yield of 50%.

Workup

  1. customThe reaction mixture obtained
  2. temperaturewas heated
  3. temperatureunder reflux for 16 hours
  4. customwas then reduced to 25° C.
  5. washThe reaction mixture was washed with water and saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. customAfter the solvent had been removed under reduced pressure
  8. customthe crude product obtained
  9. customwas purified by column chromatography (5% methanol in methylene chloride)

Sources & evidence

ORD record
ord-619a8effcbe44fa4be59cf0a8d0519c1
Source dataset
uspto-grants-2012_09
Patent number
US08268814B2

Reaction notes

Loading…