Acetic Acid → HCID 67125805, compound

HRID 2042406Notes

Reaction equation

HRID 2042406 reaction equation
[N:1]1([C:7]2[C:12]3[CH:13]=[CH:14][O:15][C:11]=3[CH:10]=[CH:9][N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(O)(=O)C.[H][H]>CO.[Pd]>[N:1]1([C:7]2[C:12]3[CH2:13][CH2:14][O:15][C:11]=3[CH:10]=[CH:9][N:8]=2)[CH2:2][CH2:3][NH:4][CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 27948084-(Piperazin-1-yl)furo[3,2-c]pyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 67125805HCID 67125805, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of commercially available 4-(piperazin-1-yl)-furo[3,2-c]pyridine [CAS-No. 81078-84-4] (1 g, 4.92 mmol), Pd/C 5% (0.46 g, 4.32 mmol), acetic acid (2.3 ml) in MeOH (6.9 ml) was stirred in a hydrogen atmosphere at room temperature for 48 h. After removal of the catalyst by filtration the mixture was evaporated, the residue was dissolved in dichloromethane/MeOH/NH4OH 80:10:1, washed with 2N sodium carbonate solution, dried (MgSO4) and evaporated. The crude material (0.68 g) was purified by chromatography on silica gel (dichloromethane/MeOH/NH4OH 80:10:1) to yield 4-(piperazin-1-yl)-2,3-dihydrofuro[3,2-c]pyridine as a white solid (0.39 g, 39%), MS (ISP) m/z=206.2 [(M+H)+], mp 89.5° C.

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration the mixture
  3. customwas evaporated
  4. dissolutionthe residue was dissolved in dichloromethane/MeOH/NH4OH 80:10:1
  5. washwashed with 2N sodium carbonate solution
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe crude material (0.68 g) was purified by chromatography on silica gel (dichloromethane/MeOH/NH4OH 80:10:1)

Sources & evidence

ORD record
ord-db3b6a8b897646cbbdfd303e8c0c9975
Source dataset
uspto-grants-2013_11
Patent number
US08586579B2

Reaction notes

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