Potassium Carbonate → HCID 14720328, compound

HRID 2351994Notes

Reaction equation

HRID 2351994 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4][NH:5][CH2:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:23][S:24](Cl)(=[O:26])=[O:25]>ClCCl>[F:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4][N:5]([CH2:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)[S:24]([CH3:23])(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 4719737HCID 4719737, compound

Product 1

HCID 14720328HCID 14720328, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 4.2 g. portion of 4-(2-fluorobenzylaminomethyl)pyridine was dissolved in 50 ml. of dichloromethane, and to it was added 3 g. of potassium carbonate and 2.5 g. of methanesulfonyl chloride. The mixture was stirred at ambient temperature for 4 days, and was then diluted with 50 ml. of water and extracted with 150 ml. of dichloromethane. The organic phase was dried over magnesium sulfate, and concentrated under vacuum. The oily residue was chromatographed on silica gel, eluting with 3:2 toluene:acetone. The product-containing fractions were evaporated to obtain an oil which solidified upon standing, and was triturated with petroleum ether to obtain 3.25 g. of the desired product, m.p. 69°-70°.

Workup

  1. additionwas then diluted with 50 ml
  2. extractionof water and extracted with 150 ml
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe oily residue was chromatographed on silica gel
  6. washeluting with 3:2 toluene
  7. customThe product-containing fractions were evaporated
  8. customto obtain an oil which
  9. customwas triturated with petroleum ether
  10. customto obtain 3.25 g

Sources & evidence

ORD record
ord-4a7e10f2adbf417db2955f947bf02686
Source dataset
uspto-grants-1989_10
Patent number
US04874775

Reaction notes

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