Potassium Carbonate → HCID 14720340, compound

HRID 2351999Notes

Reaction equation

HRID 2351999 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][CH2:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:22][S:23](Cl)(=[O:25])=[O:24]>CC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[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]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 14720339N-(2-Fluorophenyl)-3-pyridinemethanamine

Product 1

HCID 14720340HCID 14720340, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A 6 g. portion of 3-(2-fluorophenylaminomethyl)pyridine was dissolved in 50 ml. of acetone, and 5 g. of potassium carbonate and 5 g. of methanesulfonyl chloride were added. The mixture was stirred at ambient temperature overnight, and then under reflux for 6 hours. The mixture was cooled and filtered, and the filtrate was concentrated under vacuum to obtain 7.4 g. of an oil, which was chromatographed on silica gel, eluting with 1:4 acetone:toluene. Combination of the product-containing fractions and evaporation gave 9.7 g. of the desired product, m.p. 120°.

Workup

  1. temperatureunder reflux for 6 hours
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under vacuum
  5. customto obtain 7.4 g
  6. customof an oil, which was chromatographed on silica gel
  7. washeluting with 1:4 acetone
  8. customCombination of the product-containing fractions and evaporation
  9. customgave 9.7 g

Sources & evidence

ORD record
ord-f19b25a22b8e4386bda3d1ee4d251cf3
Source dataset
uspto-grants-1989_10
Patent number
US04874775

Reaction notes

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