Potassium Carbonate → HCID 14720306, compound

HRID 2351979Notes

Reaction equation

HRID 2351979 reaction equation
[C:1]1([CH2:7][CH2:8][NH:9][CH2:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:17][S:18](Cl)(=[O:20])=[O:19].C(=O)([O-])[O-].[K+].[K+]>ClCCl>[C:1]1([CH2:7][CH2:8][N:9]([CH2:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[S:18]([CH3:17])(=[O:20])=[O:19])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 201619Phenethyl-pyridin-3-ylmethyl-amine

Product 1

HCID 14720306HCID 14720306, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 4.4 g. portion of 3-(2-phenylethyl)aminomethylpyridine was reacted with 2.4 g. of methanesulfonyl chloride in the presence of 4 g. of potassium carbonate in 60 ml. of dichloromethane at ambient temperature for several days. The mixture was then diluted with 100 ml. of dichloromethane and extracted with 50 ml. of water. The organic layer was dried over magnesium sulfate and concentrated under vacuum. The residue was taken up in toluene and chromatographed on silica gel, eluting with 9:1 toluene:acetone. The product-containing fractions were combined and evaporated under vacuum, and the residue solidified on standing. The solids were triturated in ether and dried to obtain 1.8 g. of the desired product, m.p. 94°-95°.

Workup

  1. additionThe mixture was then diluted with 100 ml
  2. extractionof dichloromethane and extracted with 50 ml
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under vacuum
  5. customchromatographed on silica gel
  6. washeluting with 9:1 toluene
  7. customevaporated under vacuum
  8. customThe solids were triturated in ether
  9. customdried
  10. customto obtain 1.8 g

Sources & evidence

ORD record
ord-71638357ae604c3aa314ac9046ea976c
Source dataset
uspto-grants-1989_10
Patent number
US04874775

Reaction notes

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