Acetic Acid → HCID 51263596, compound

HRID 1910781Notes

Reaction equation

HRID 1910781 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:16]([OH:19])(=O)[CH3:17].O.C([BH3-])#N.[Na+].[CH2:25]1[CH2:29]OC[CH2:26]1>>[O:19]1[CH:29]=[CH:25][CH:26]=[C:16]1[CH2:17][N:13]1[CH2:14][CH2:15][N:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)[CH2:11][CH2:12]1

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 962WaterHCID 8028TetrahydrofuranHCID 804471-(4-Nitrophenyl)piperazineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 51263596HCID 51263596, compoundYield 54%

Procedure

To a solution of 1-(4-nitrophenyl)-piperazine (0.6 g, 2.89 mmol) in THF (10 mL) was added fufaraldehyde (0.41 g, 4.31 mmol), acetic acid (3 mL) and water (1.5 mL) and the mixture stirred at r.t. for half an hour. Sodium cyanoborohydride (0.27 g, 4.31 mmol) was added and the reaction heated at reflux for four hours. The reaction was cooled and the solvent evaporated. The resulting residue was diluted with water and extracted with dichloromethane. The combined organic layers were washed with saturated sodium bicarbonate and brine solution, dried over sodium sulfate, filtered and concentrated. Purification by column chromatography over silica gel (60-120 mesh) using 5% methanol/chloroform as eluent afforded 1-furan-2-ylmethyl-4-(4-nitrophenyl)-piperazine (0.45 g, 54%) as a yellow solid.

Workup

  1. temperaturethe reaction heated
  2. temperatureat reflux for four hours
  3. temperatureThe reaction was cooled
  4. customthe solvent evaporated
  5. additionThe resulting residue was diluted with water
  6. extractionextracted with dichloromethane
  7. washThe combined organic layers were washed with saturated sodium bicarbonate and brine solution
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customPurification by column chromatography over silica gel (60-120 mesh)

Sources & evidence

ORD record
ord-dfd454b330d14f3799d0027c4b512596
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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