Sodium Iodide → HCID 15105344, compound

HRID 2253677Notes

Reaction equation

HRID 2253677 reaction equation
Cl[CH2:2][CH2:3][N:4]1[C:12](=[O:13])[N:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C:6]2=[N:5]1.[I-].[Na+].[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)=[C:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:36][C:33]1[CH:34]=[CH:35][C:30]([C:23]([C:20]2[CH:19]=[CH:18][C:17]([F:16])=[CH:22][CH:21]=2)=[C:24]2[CH2:29][CH2:28][N:27]([CH2:2][CH2:3][N:4]3[C:12](=[O:13])[N:7]4[CH2:8][CH2:9][CH2:10][CH2:11][C:6]4=[N:5]3)[CH2:26][CH2:25]2)=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 27244364-(Bis(4-fluorophenyl)methylene)piperidineHCID 15105335HCID 15105335, compound

Product 1

HCID 15105344HCID 15105344, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-(2-Chloroethyl)-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a]pyridin-3(2H)-one (26.8 g), 31.5 g of sodium iodide and 400 mλ of acetonitrile were refluxed for 30 minutes. To the reaction mixture were added 38.2 g of 4-[bis(4-fluorophenyl)methylene]piperidine and 27.6 g of potassium carbonate, followed by heating at reflux for 8 hours. The insoluble material was removed by filtration, and the filtrate was concentrated to dryness under reduced pressure. The residue was dissolved in 200 mλ of chloroform, and the solution was applied to a column contained with 550 g of silica gel and eluted with chloroform to obtain 53.0 g of the entitled compound as an oily substance.

Workup

  1. temperatureby heating
  2. temperatureat reflux for 8 hours
  3. customThe insoluble material was removed by filtration
  4. concentrationthe filtrate was concentrated to dryness under reduced pressure
  5. dissolutionThe residue was dissolved in 200 mλ of chloroform
  6. washeluted with chloroform

Sources & evidence

ORD record
ord-67e46879b8ff428c8248d660fe4aac50
Source dataset
uspto-grants-1993_08
Patent number
US05232924

Reaction notes

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