1H-1,2,4-Triazole → HCID 23284976, compound

HRID 369190Notes

Reaction equation

HRID 369190 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.C(=O)([O-])[O-].[K+].[K+].[CH3:12][N:13]([CH:22]1[CH2:27][CH2:26][N:25]([C:28](=[O:36])[C:29]2[CH:34]=[CH:33][C:32](Cl)=[N:31][CH:30]=2)[CH2:24][CH2:23]1)[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CS(C)=O>[CH3:12][N:13]([CH:22]1[CH2:27][CH2:26][N:25]([C:28](=[O:36])[C:29]2[CH:34]=[CH:33][C:32]([N:1]3[CH:5]=[N:4][CH:3]=[N:2]3)=[N:31][CH:30]=2)[CH2:24][CH2:23]1)[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 23285053HCID 23285053, compound

Product 1

HCID 23284976HCID 23284976, compoundYield 15.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

1.16 g of 1,2,4-triazole and 1.16 g of potassium carbonate were added to a solution of 2.00 g of 4-[N-methyl-N-(2-phenylethyl)amino]-1-(6-chloronicotinoyl)piperidine in 10 ml of dimethyl sulfoxide. The container inside was purged with nitrogen and the container contents were stirred at 100° C. for 4 hours. The reaction mixture was cooled and water was added thereto. The mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was purified by a silica gel column chromatography (eluant: methylene chloride/methanol=150/1). The product was subjected to crystallization from diethyl ether and then to recrystallization from ethyl acetate-diethyl ether to obtain 0.33 g of 4-[N-methyl-N-(2-phenylethyl)amino]-1-[6-(1,2,4-triazol-1-yl)nicotinoyl]piperidine as a white powder.

Workup

  1. customThe container inside was purged with nitrogen
  2. temperatureThe reaction mixture was cooled
  3. additionwater was added
  4. extractionThe mixture was extracted with ethyl acetate
  5. washThe extract was washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried with anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by a silica gel column chromatography (eluant: methylene chloride/methanol=150/1)
  9. customThe product was subjected to crystallization from diethyl ether
  10. customto recrystallization from ethyl acetate-diethyl ether

Sources & evidence

ORD record
ord-d1c7aa17f129405fb94f5904bba3b5fa
Source dataset
uspto-grants-2000_10
Patent number
US06136826

Reaction notes

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