Methanol → 1-(4-Fluorophenyl)-4-methyl-1H-1,2,3-triazole

HRID 2365219Notes

Reaction equation

HRID 2365219 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12](N3CCCCC3)[CH:11]([CH3:19])[N:10]=[N:9]2)=[CH:4][CH:3]=1.[OH-].[K+].CO>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[C:11]([CH3:19])[N:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 199146541-(4-Fluorophenyl)-4-methyl-5-piperidino-4,5-dihydro-1,2,3-triazole

Product 1

HCID 199146881-(4-Fluorophenyl)-4-methyl-1H-1,2,3-triazoleYield 78.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Prepared in analogy to EP 0 433 842 A2. A mixture of 1-[3-(4-fluoro-phenyl)-5-methyl-4,5-dihydro-3H-[1,2,3]triazol-4-yl]-piperidine (1.15 g, 0.004 mol) and potassium hydroxide in MeOH (2 N, 29.2 mL, 58 mmol) was heated under reflux for 6 h then cooled to room temperature. The mixture was then poured into water and extracted with diethyl ether and the combined organic extracts washed with brine, dried over sodium sulphate, filtered and evaporated to give the title product (555 mg) as a white solid. The filtrate was evaporated and purification by chromatography (silica, 10 to 60% ethyl acetate in heptane) afforded the title compound (41 mg, 79%) as an off white solid. Total yield (596 mg, 77%). MS: m/e=178.1 [M+H]+.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 h
  3. extractionextracted with diethyl ether
  4. washthe combined organic extracts washed with brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-19abcc50ff014e859e50bdd37b4b7c9c
Source dataset
uspto-grants-2014_04
Patent number
US08697696B2

Reaction notes

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