Potassium Carbonate → N-(1-methylhexyl)-N-(pyridin-3-ylmethyl)methanesulfonamide

HRID 2351966Notes

Reaction equation

HRID 2351966 reaction equation
[CH3:1][CH:2]([NH:8][CH2:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C(=O)([O-])[O-].[K+].[K+].[CH3:22][S:23](Cl)(=[O:25])=[O:24]>ClCCl>[CH3:1][CH:2]([N:8]([CH2:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)[S:23]([CH3:22])(=[O:25])=[O:24])[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 147202823-(1-Methylhexylaminomethyl)pyridine

Product 1

HCID 14720283N-(1-methylhexyl)-N-(pyridin-3-ylmethyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 3.1 g. portion of 3-(1-methylhexylaminomethyl)pyridine was dissolved in dichloromethane with stirring, and to it were added 2.1 g. of potassium carbonate and 1.16 ml. of methanesulfonyl chloride with cooling in an ice bath. The mixture was stirred at ambient temperature for 4 days. The reaction mixture was then extracted twice with 15 ml. portions of water, and the organic layer was dried over magnesium sulfate, filtered and evaporated under vacuum. The residue was dissolved in ethyl acetate and purified by chromatography over silica gel in ethyl acetate. The product-containing fractions were combined to obtain 1.7 g. of the desired product. Elemental analysis:

Workup

  1. additionto it were added 2.1 g
  2. stirringThe mixture was stirred at ambient temperature for 4 days
  3. extractionThe reaction mixture was then extracted twice with 15 ml
  4. dry with materialportions of water, and the organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under vacuum
  7. dissolutionThe residue was dissolved in ethyl acetate
  8. custompurified by chromatography over silica gel in ethyl acetate
  9. customto obtain 1.7 g

Sources & evidence

ORD record
ord-d06d1e6648d04f52a36f349be1e16151
Source dataset
uspto-grants-1989_10
Patent number
US04874775

Reaction notes

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