Potassium Iodide → HCID 22557840, compound

HRID 395422Notes

Reaction equation

HRID 395422 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:18]=[C:17]([CH2:19][O:20][CH:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[CH:16]=[CH:15][N:14]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[Cl:27][CH2:28][C:29]1[CH:34]=[CH:33][N:32]=[C:31]([C:35]2[CH:40]=[C:39]([O:41][CH3:42])[C:38]([O:43][CH3:44])=[C:37]([O:45][CH3:46])[CH:36]=2)[CH:30]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[ClH:27].[ClH:27].[ClH:27].[CH3:42][O:41][C:39]1[CH:40]=[C:35]([C:31]2[CH:30]=[C:29]([CH2:28][N:24]3[CH2:23][CH2:22][CH:21]([O:20][CH2:19][C:17]4[CH:16]=[CH:15][N:14]=[C:13]([C:5]5[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=5)[CH:18]=4)[CH2:26][CH2:25]3)[CH:34]=[CH:33][N:32]=2)[CH:36]=[C:37]([O:45][CH3:46])[C:38]=1[O:43][CH3:44]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 120192374-Chloromethyl-2-(3,4,5-trimethoxyphenyl) pyridineHCID 12043124HCID 12043124, compound

Product 1

HCID 22557840HCID 22557840, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyloxy]piperidine (70 mg), 4-chloromethyl-2-(3,4,5-trimethoxyphenyl)pyridine (22 mg), potassium carbonate (56 mg) and potassium iodide (40 mg) were suspended in acetonitrile (5 mL). The mixture was stirred at room temperature for 5 hr and evaporated. Chloroform and water were added to the residual oil and the organic layer was separated. Aqueous layer was then extracted with chloroform and the organic layers were combined, dried over anhydrous magnesium sulfate and evaporated. The residue was applied to a column of silica gel using chloroform-methanol (40:1) as an eluent. Fractions containing the product were collected and evaporated. The title compound was obtained by converting the free base to a trihydrochloride.

Workup

  1. customevaporated
  2. additionChloroform and water were added to the residual oil
  3. customthe organic layer was separated
  4. extractionAqueous layer was then extracted with chloroform
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated
  7. additionFractions containing the product
  8. customwere collected
  9. customevaporated

Sources & evidence

ORD record
ord-1bb89d7e401a4ecab4b703da8f3de807
Source dataset
uspto-grants-2003_08
Patent number
US06605620B1

Reaction notes

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