Potassium Carbonate → Methyl 6-(2-(piperidin-1-yl)ethoxy)benzofuran-2-carboxylate

HRID 1907762Notes

Reaction equation

HRID 1907762 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:5]2[CH:6]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[O:8][C:4]=2[CH:3]=1.Cl[CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CC(C)=O.CCOC(C)=O>[N:18]1([CH2:17][CH2:16][O:1][C:2]2[CH:14]=[CH:13][C:5]3[CH:6]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[O:8][C:4]=3[CH:3]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 748271-(2-Chloroethyl)piperidineHCID 12082972Methyl 6-hydroxy-1-benzofuran-2-carboxylate

Product 1

HCID 59737221Methyl 6-(2-(piperidin-1-yl)ethoxy)benzofuran-2-carboxylateYield 60%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 394 (350 mg, 1.82 mmol), 1-(2-Chloroethyl)piperidine (269 mg, 1.82 mmol) and K2CO3 (503 mg, 3.64 mmol) in DMF (10 mL) and acetone (10 mL) was stirred at 60° C. for 3 h and then at room temperature for 3 days (or until completion). The crude product was dissolved in AcOEt and washed with water. The organic layer was separated and dried with Na2SO4, filtered and concentrated under vacuum. The residue was purified via Isco (0-25% MeOH/EtOAc) to afford the title compound 395 as a white solid (330 mg, 60% yield).

Workup

  1. washwashed with water
  2. customThe organic layer was separated
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified via Isco (0-25% MeOH/EtOAc)

Sources & evidence

ORD record
ord-c0bad20b8f114ec18e6ffc11eee3d30a
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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