Acetic Acid → 7-(Piperazin-1-yl)-2,3-dihydro-furo[2,3-c]pyridine

HRID 1260703Notes

Reaction equation

HRID 1260703 reaction equation
[N:1]1([C:7]2[N:8]=[CH:9][CH:10]=[C:11]3[CH:15]=[CH:14][O:13][C:12]=23)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(O)(=O)C.[H][H]>CO.[Pt](=O)=O>[N:1]1([C:7]2[N:8]=[CH:9][CH:10]=[C:11]3[CH2:15][CH2:14][O:13][C:12]=23)[CH2:2][CH2:3][NH:4][CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 183997267-(Piperazin-1-yl)furo[2,3-c]pyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 666534657-(Piperazin-1-yl)-2,3-dihydro-furo[2,3-c]pyridineYield 95.1%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A mixture of 7-(piperazin-1-yl)-furo[2,3-c]pyridine [CAS-No. 209160-83-8] (1 g, 4.92 mmol), platinum(IV) oxide (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 24 h. After removal of the catalyst by filtration the mixture was evaporated, the residue was dissolved in dichloromethane (70 ml), washed with 2N sodium carbonate solution (40 ml), dried (MgSO4) and evaporated to yield 7-(piperazin-1-yl)-2,3-dihydro-furo[2,3-c]pyridine as a light brown oil (0.96 g, 95%), MS (ISP) m/z=206.3 [(M+H)+].

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration the mixture
  3. customwas evaporated
  4. dissolutionthe residue was dissolved in dichloromethane (70 ml)
  5. washwashed with 2N sodium carbonate solution (40 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-24c4648e993e4d1a967905598725e451
Source dataset
uspto-grants-2013_06
Patent number
US08470828B2

Reaction notes

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