Methyl iodide → 5-chloro-3-methyl-6-(piperidin-1-yl)-benzofuran-2(3H)-one

HRID 2295816Notes

Reaction equation

HRID 2295816 reaction equation
[Cl:1][C:2]1[C:3]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:4][C:5]2[O:9][C:8](=[O:10])[CH2:7][C:6]=2[CH:11]=1.[CH3:18]I.[H-].[Na+]>COCCOC>[Cl:1][C:2]1[C:3]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:4][C:5]2[O:9][C:8](=[O:10])[CH:7]([CH3:18])[C:6]=2[CH:11]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 135769525-chloro-6-(piperidin-1-yl)-benzofuran-2(3H)-one

Product 1

HCID 135769475-chloro-3-methyl-6-(piperidin-1-yl)-benzofuran-2(3H)-one

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

A solution of 2.5 g (10 mmoles) of 5-chloro-6-(piperidin-1-yl)-benzofuran-2(3H)-one and 2.1 g (15 mmoles) of methyl iodide in 15 ml of absolute 1,2-dimethoxyethane is added dropwise in the course of 20 minutes to a suspension, boiling under nitrogen, of 530 mg (11 mmoles) of 50% strength sodium hydride-oil dispersion in 15 ml of absolute 1,2-dimethoxyethane. The mixture is then boiled under reflux for a further 3 hours, the solvent is removed in vacuo and the residue is cautiously acidified with dilute hydrochloric acid and extracted three times with methylene chloride. The organic phases are washed with water, combined, dried over sodium sulphate and concentrated in a vacuum rotary evaporator. Recrystallisation from ether/petroleum ether yields 5 -chloro-3-methyl-6-(piperidin-1-yl)-benzofuran-2(3H)-one having a melting point of 112°-113°.

Workup

  1. temperatureunder reflux for a further 3 hours
  2. customthe solvent is removed in vacuo
  3. extractionextracted three times with methylene chloride
  4. washThe organic phases are washed with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in a vacuum rotary evaporator
  7. customRecrystallisation from ether/petroleum ether

Sources & evidence

ORD record
ord-08189b46695e44378c6b8a032d84c6e2
Source dataset
uspto-grants-1984_01
Patent number
US04426380

Reaction notes

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