Dichloromethane → HCID 14720304, compound

HRID 2351978Notes

Reaction equation

HRID 2351978 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][CH2:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.ClCCl.C(=O)([O-])[O-].[K+].[K+].[CH3:27][S:28](Cl)(=[O:30])=[O:29]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][N:10]([CH2:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[S:28]([CH3:27])(=[O:30])=[O:29])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6344Dichloromethane2×HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 28512782-(4-chlorophenyl)-N-(pyridin-4-ylmethyl)ethanamine

Product 1

HCID 14720304HCID 14720304, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 7.4 g. portion of 4-[2-(4-chlorophenyl)ethylaminomethyl]pyridine was dissolved in 50 ml. of dichloromethane, and to it were added 4 g. of potassium carbonate and 4 g. of methanesulfonyl chloride. The mixture was stirred at ambient temperature overnight, and then 100 ml. of additional dichloromethane was added, followed by 200 ml. of water. The organic phase was separated, washed with water, dried and concentrated under vacuum. The residue was chromatographed on silica gel, using acetone as the eluant. The product-containing fractions were combined and evaporated, and the residue crystallized upon standing. The solids were triturated with petroleum ether and filtered and dried to obtain 4.0 g. of the desired product, m.p. 96°-99°.

Workup

  1. customThe organic phase was separated
  2. washwashed with water
  3. customdried
  4. concentrationconcentrated under vacuum
  5. customThe residue was chromatographed on silica gel
  6. customevaporated
  7. customthe residue crystallized
  8. customThe solids were triturated with petroleum ether
  9. filtrationfiltered
  10. customdried
  11. customto obtain 4.0 g

Sources & evidence

ORD record
ord-91e9b6dad34c42f78479929c3226a7b5
Source dataset
uspto-grants-1989_10
Patent number
US04874775

Reaction notes

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