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

HRID 1164513Notes

Reaction equation

HRID 1164513 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1.[H-].[Na+].[CH:13]1([S:19](Cl)(=[O:21])=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>CN(C)C=O.C(O)C>[CH3:1][N:2]([CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1)[S:19]([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)(=[O:21])=[O:20]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 143276Methyl[2-(pyridin-4-yl)ethyl]amineHCID 237554Cyclohexanesulfonyl chloride

Product 1

HCID 20511183N-methyl-N-(2-[4-pyridyl]ethyl)cyclohexanesulphonamideYield 83.6%

Reagents, catalysts & solvents 2

HCID 702EthanolCatalystHCID 6228DimethylformamideSolvent

Procedure

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°.

Workup

  1. temperatureUpon gentle warming to 50° for 1 hour the coloured anion
  2. temperatureAfter cooling to 0°
  3. filtrationfiltered
  4. extractionextracted with chloroform (25 ml×4)
  5. dry with materialthe organic phase dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. distillationResidual DMF was distilled from the product at 0.7 mm.Hg
  8. customthe remaining viscous oil column-chromatographed upon silica (150 g) by elution with chloroform
  9. customEvaporation of the primary fractions (200 ml×3)

Sources & evidence

ORD record
ord-135a79974db04d22b02c4a824e3619bd
Source dataset
uspto-grants-1983_01
Patent number
US04370328

Reaction notes

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