Methyl iodide → 5-chloro-3-methyl-6-(piperidin-1-yl)-benzofuran-2(3H)-one
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]=1Participants
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
- temperatureunder reflux for a further 3 hours
- customthe solvent is removed in vacuo
- extractionextracted three times with methylene chloride
- washThe organic phases are washed with water
- dry with materialdried over sodium sulphate
- concentrationconcentrated in a vacuum rotary evaporator
- customRecrystallisation from ether/petroleum ether
Sources & evidence
- ORD record
- ord-a6bbc8bc48c8445ab1e7ef81ee7c2848
- Source dataset
- uspto-grants-1984_05
- Patent number
- US04451462
Reaction notes
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