Sodium hydride → N-methyl-N-(2-[4-pyridyl]ethyl)cyclohexanesulphonamide

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Reaction Steps

N-Methyl-2-(4-pyridyl)ethylamine (5 g) was added dropwise over 15 minutes to a stirred suspension of sodium hydride (1.77 g, 50% dispersion in oil) in dry N,N-dimethylformamide (80 ml) (DMF) containing absolute ethanol (2 drops) under dry nitrogen at room temperature. Upon gentle warming to 50° for 1 hour the coloured anion was generated. After cooling to 0°, cyclohexanesulphonyl chloride (6.71 g) was added dropwise over 45 minutes then the stirred mixture allowed to attain room temperature over 18 hours. The yellow solution was then added to ice-water (200 ml), filtered, extracted with chloroform (25 ml×4), the organic phase dried (MgSO4) and concentrated in vacuo. Residual DMF was distilled from the product at 0.7 mm.Hg and the remaining viscous oil column-chromatographed upon silica (150 g) by elution with chloroform. Evaporation of the primary fractions (200 ml×3) afforded crystalline N-methyl-N-(2-[4-pyridyl]ethyl)cyclohexanesulphonamide (8.67 g), m.p. 94°- 6°.

Provenance & Evidence