Potassium Carbonate → N-cyclohexyl-N-(pyridin-3-ylmethyl)-methanesulfonamide

HRID 2351985Notes

Reaction equation

HRID 2351985 reaction equation
[CH:1]1([NH:7][CH2:8][C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[CH3:21][S:22](Cl)(=[O:24])=[O:23]>ClCCl>[CH:1]1([N:7]([CH2:8][C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[S:22]([CH3:21])(=[O:24])=[O:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 757273N-(pyridin-3-ylmethyl)cyclohexanamine

Product 1

HCID 14720315N-cyclohexyl-N-(pyridin-3-ylmethyl)-methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 2.85 g. portion of 3-cyclohexylaminomethylpyridine was dissolved in 15 ml. of dichloromethane, and 2.8 g. of potassium carbonate and 1.6 ml. of methanesulfonyl chloride were added. The mixture boiled vigorously for a short time, and was then stirred at ambient temperature overnight. The mixture was diluted with 25 ml. of additional dichloromethane, and was extracted with 20 ml. of water and dried over magnesium sulfate. The organic solution was reduced in volume and chromatographed over silica gel, eluting first with dichloromethane and then with 9:1 dichloromethane:ethyl acetate. The product-containing fractions were evaporated under vacuum, and the residue was triturated with petroleum ether and diethyl ether to obtain 0.8 g. of the desired product.

Workup

  1. additionThe mixture was diluted with 25 ml
  2. extractionof additional dichloromethane, and was extracted with 20 ml
  3. dry with materialof water and dried over magnesium sulfate
  4. customchromatographed over silica gel
  5. washeluting first with dichloromethane
  6. customThe product-containing fractions were evaporated under vacuum
  7. customthe residue was triturated with petroleum ether and diethyl ether
  8. customto obtain 0.8 g

Sources & evidence

ORD record
ord-bd02822d46ad4ac581a0bd5463ed6f13
Source dataset
uspto-grants-1989_10
Patent number
US04874775

Reaction notes

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