Piperidine → 3-Cyclopropyl-4-[(4,5-dimethylpyrrol-2-yl)methylene]-2-pyrazolin-5-one

HRID 1828885Notes

Reaction equation

HRID 1828885 reaction equation
[CH:1]1([C:4]2[CH2:8][C:7](=[O:9])[NH:6][N:5]=2)[CH2:3][CH2:2]1.[CH3:10][C:11]1[CH:12]=[C:13]([CH:17]=O)[NH:14][C:15]=1[CH3:16].N1CCCCC1>C(O)C>[CH:1]1([C:4]2[C:8](=[CH:17][C:13]3[NH:14][C:15]([CH3:16])=[C:11]([CH3:10])[CH:12]=3)[C:7](=[O:9])[NH:6][N:5]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 5789704,5-Dimethyl-1H-pyrrole-2-carbaldehydeHCID 220594943-cyclopropyl-4,5-dihydro-1H-pyrazol-5-one

Product 1

HCID 1363565383-Cyclopropyl-4-[(4,5-dimethylpyrrol-2-yl)methylene]-2-pyrazolin-5-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A reaction mixture of 3-cyclopropyl-2-pyrazolin-5-one (790 mg, 6.3 mmol), 4,5-dimethylpyrrole-2-carboxaldehyde (800 mg, 6.5 mmol), and piperidine 100 mg, in ethanol 50 mL was stirred at 90° C. for 3.5 h. The solvent was removed under reduced pressure. The solid residue was purified by flash column chromatography using (3:7) ethyl acetate:hexane as the mobile phase, then further purified by recrystallization from toluene.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe solid residue was purified by flash column chromatography
  3. customhexane as the mobile phase, then further purified by recrystallization from toluene

Sources & evidence

ORD record
ord-727f2a5e88624356b4b60699002a4b69
Source dataset
uspto-grants-2006_06
Patent number
US07060822B1

Reaction notes

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