4-Pyridineacetic acid → HCID 18715055, compound

HRID 494018Notes

Reaction equation

HRID 494018 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]([OH:10])=O)=[CH:3][CH:2]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:23][N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1>O1CCCC1>[O:10]=[C:8]([N:27]1[CH2:28][CH2:29][N:24]([CH3:23])[CH2:25][CH2:26]1)[CH2:7][C:4]1[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 342284-Pyridineacetic acidHCID 531671-MethylpiperazineHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 18715055HCID 18715055, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution is prepared of 3 g (17.3 mM) of (4-pyridinyl)acetic acid in 50 ml of tetrahydrofuran (THF) and, at ambient temperature, a solution of 3.4 g (20.7 mM) of carbonyldiimidazole in solution in 50 ml of THF, is added dropwise. The reaction mixture is agitated for 8 hours, and a solution of 1.73 g (17.3 mM) of N-methylpiperazine in 20 ml of THF is then added. The reaction mixture is heated under reflux of the solvent for 2 hours, and then concentrated under reduced pressure. The residue from evaporation is taken up with 80 ml of 3N sodium hydroxide and extracted with ethyl acetate. The organic phase is dried over magnesium sulphate and concentrated under reduced pressure. The crude product is purified by silica gel chromatography in eluting with the aid of a dichloromethane/methanol mixture (99/1; v/v). The product sought after is obtained as a colourless oil (yield=28%).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux of the solvent for 2 hours
  3. concentrationconcentrated under reduced pressure
  4. customThe residue from evaporation
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic phase is dried over magnesium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product is purified by silica gel chromatography
  9. washin eluting with the aid of a dichloromethane/methanol mixture (99/1; v/v)

Sources & evidence

ORD record
ord-bd8f348b850b46b79e5bfc1a84a02dd2
Source dataset
uspto-grants-2009_05
Patent number
US07538111B2

Reaction notes

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