Potassium Iodide → [1-(4-Methyl-3-pentenyl)piperidin-4-yl] 2-cyclobutyl-2-hydroxy-2-phenylacetate

HRID 1289807Notes

Reaction equation

HRID 1289807 reaction equation
Cl.[CH:2]1([C:6]([OH:22])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:7]([O:9][CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[O:8])[CH2:5][CH2:4][CH2:3]1.Br[CH2:24][CH2:25][CH:26]=[C:27]([CH3:29])[CH3:28].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH:2]1([C:6]([OH:22])([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:7]([O:9][CH:10]2[CH2:11][CH2:12][N:13]([CH2:24][CH2:25][CH:26]=[C:27]([CH3:29])[CH3:28])[CH2:14][CH2:15]2)=[O:8])[CH2:5][CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 1375215-Bromo-2-methyl-2-penteneHCID 69831797(Piperidin-4-yl) 2-cyclobutyl-2-hydroxy-2-phenylacetate hydrochloride

Product 1

HCID 18922143[1-(4-Methyl-3-pentenyl)piperidin-4-yl] 2-cyclobutyl-2-hydroxy-2-phenylacetateYield 61.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

50 mg of (piperidin-4-yl) 2-cyclobutyl-2-hydroxy-2-phenylacetate hydrochloride, 25 mg of 5-bromo-2-methyl-2-pentene, 25 mg of potassium iodide and 47 mg of anhydrous potassium carbonate were suspended in 5 ml of anhydrous N,N-dimethylformamide, and this suspension was stirred at 70° C. for 3 hours. The reaction mixture was cooled to room temperature, mixed with water, and then extracted with diethyl ether. The organic layer was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography (developing solvent: chloroform/methanol=20/1) to obtain 35 mg of the title compound.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with diethyl ether
  3. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationAfter the solvent was distilled off under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (developing solvent: chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-5a69668bbdd94a21845f8b021fa41096
Source dataset
uspto-grants-1998_05
Patent number
US05750540

Reaction notes

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