Methyl iodide → HCID 57964838, compound

HRID 2403526Notes

Reaction equation

HRID 2403526 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([CH2:11][CH2:12][N:13]3[CH2:18][CH2:17][N:16]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][OH:26])[CH:20]=4)[CH2:15][CH2:14]3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[F-].[K+].I[CH3:30].[OH-].[K+]>CS(C)=O>[O:4]1[C:5]2([CH2:10][CH2:9][CH:8]([CH2:11][CH2:12][N:13]3[CH2:14][CH2:15][N:16]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][O:26][CH3:30])[CH:20]=4)[CH2:17][CH2:18]3)[CH2:7][CH2:6]2)[O:1][CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 522689Potassium FluorideHCID 57964191HCID 57964191, compound

Product 1

HCID 57964838HCID 57964838, compoundYield 23.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 1.2 g (3.42 mmol) of 1-[2-(1,4-dioxaspiro[4.5]dec-8-yl)ethyl]-4-(3-hydroxymethylphenyl)piperazine (preparation A) in 15 mL of dimethyl sulfoxide are added, at room temperature, 1.0 g (17.2 mmol) of potassium fluoride, 0.52 g (3.66 mmol) of iodomethane and 0.68 g (10.3 mmol) of potassium hydroxide. The mixture is stirred overnight at room temperature, partitioned between with ethyl acetate and water. The aqueous phase is separated and the organic phase is washed with water, dried over magnesium sulfate, filtered and concentrated. The oily residue is purified by chromatography over silica gel (eluant hetane/ethyl acetate 1/1) to give 0.3 g of 1-[2-(1,4-dioxaspiro[4.5]dec-8-yl)ethyl]-4-(3-methoxymethylphenyl)piperazine as an oil.

Workup

  1. additionare added, at room temperature
  2. custompartitioned between with ethyl acetate and water
  3. customThe aqueous phase is separated
  4. washthe organic phase is washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe oily residue is purified by chromatography over silica gel (eluant hetane/ethyl acetate 1/1)

Sources & evidence

ORD record
ord-a5435f4ad0ac43d591f61a7daede8109
Source dataset
uspto-grants-2014_08
Patent number
US08802678B2

Reaction notes

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