1H-1,2,4-Triazole → HCID 71226656, compound

HRID 2409891Notes

Reaction equation

HRID 2409891 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH2:11][CH:10]([OH:14])[CH2:9]2)=[CH:4][CH:3]=1.[NH:15]1[CH:19]=[N:18][CH:17]=[N:16]1.CN[C@@H]1CCCC[C@H]1NC.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.[Cu]I>[N:15]1([C:2]2[CH:7]=[CH:6][C:5]([N:8]3[CH2:13][CH2:12][CH2:11][CH:10]([OH:14])[CH2:9]3)=[CH:4][CH:3]=2)[CH:19]=[N:18][CH:17]=[N:16]1

Participants

7

Reactant 4

HCID 92571H-1,2,4-TriazoleHCID 62657Potassium Phosphate, TribasicHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 71226932HCID 71226932, compound

Product 1

HCID 71226656HCID 71226656, compoundYield 61.2%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a mixture of 1-(4-iodophenyl)piperidin-3-ol (920 mg, 3.03 mmol), 1H-1,2,4-triazole (272 mg, 3.95 mmol), (trans)-N1,N2-dimethylcyclohexane-1,2-diamine (43.2 mg, 0.303 mmol), K3PO4 (1288 mg, 6.07 mmol) and copper(I) iodide (28.9 mg, 0.152 mmol) in DMF (4 mL) was bubbled with Argon for 2 min. Then the reaction was stirred at 110° C. under Argon for 16 hrs. The reaction was diluted water and extracted with EtOAc (2×50 ml). Combined EtOAc extracts were washed with water (30 ml) and saturated aqueous NaCl (30 ml). The organic layer was dried over Na2SO4, filtered and concentrated. The resulting residue was purified using silica gel chromatography (ISCO system) eluting with a gradient of 0-100% EtOAc/Hex to give product 1-(4-(1H-1,2,4-triazol-1-yl)phenyl)piperidin-3-ol (453 mg, 1.854 mmol, 61.1% yield) as a foam. Anal. Calcd. for C13H16N4O m/z 244.2, found: 245.0 (M+H)+.

Workup

  1. customwas bubbled with Argon for 2 min
  2. extractionextracted with EtOAc (2×50 ml)
  3. washCombined EtOAc extracts were washed with water (30 ml) and saturated aqueous NaCl (30 ml)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified
  8. washeluting with a gradient of 0-100% EtOAc/Hex

Sources & evidence

ORD record
ord-a44fc9278a3d4f90950f2de29dee6d2d
Source dataset
uspto-grants-2014_08
Patent number
US08815909B2

Reaction notes

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