Ethyl Acetate → HCID 66584436, compound

HRID 2174696Notes

Reaction equation

HRID 2174696 reaction equation
S(O[CH2:12][CH2:13][CH2:14][CH:15]1[CH2:20][CH2:19][N:18]([C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)[CH2:17][CH2:16]1)(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].[NH:36]1[CH:40]=[N:39][CH:38]=[N:37]1.C(OCC)(=O)C>C(#N)C>[N:36]1([CH2:12][CH2:13][CH2:14][CH:15]2[CH2:16][CH2:17][N:18]([C:21]3[CH:22]=[CH:23][C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=3)[CH2:19][CH2:20]2)[CH:40]=[N:39][CH:38]=[N:37]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 86660670HCID 86660670, compound

Product 1

HCID 66584436HCID 66584436, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

The 4-tosyloxypropyl-N-(4-nitrophenyl)piperidine (4.19 g, 10.0 mmol) obtained in Example 11(2) was dissolved in acetonitrile (40 ml), and potassium carbonate (2.76 g, 20 mmol) and 1,2,4-triazole (1.04 g, 15.0 mmol) were added thereto, followed by stirring at 80° C. for 18 hours. After the reaction mixture was allowed to cool to room temperature, ethyl acetate was added to the reaction mixture, and the organic layer was washed with water and saturated sodium chloride, and dried over anhydrous sodium sulfate. After the desiccant was filtered off, the residue obtained by evaporation under reduced pressure was purified using medium pressure silica gel flash column chromatography (methanol:chloroform=1:100 to 1:30), thereby obtaining 4-[3-(1,2,4-triazol-1-yl)-propyl]-N-(4-nitrophenyl)piperidine (2.47 g, 78%) as a yellow solid.

Workup

  1. temperatureto cool to room temperature
  2. washthe organic layer was washed with water and saturated sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter the desiccant was filtered off
  5. customthe residue obtained by evaporation under reduced pressure
  6. customwas purified

Sources & evidence

ORD record
ord-2d730b9e940b467f8c85dc011feae8d7
Source dataset
uspto-grants-2015_06
Patent number
US09062035B2

Reaction notes

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