Water → N-(12-Iodododecyl)-6-(4-ethyl-1-piperazinyl)pyridine-3-carboxamide

HRID 1003296Notes

Reaction equation

HRID 1003296 reaction equation
S(O[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19]([C:21]1[CH:22]=[N:23][C:24]([N:27]2[CH2:32][CH2:31][N:30]([CH2:33][CH3:34])[CH2:29][CH2:28]2)=[CH:25][CH:26]=1)=[O:20])(C)(=O)=O.[I-:35].[Na+].O.C(Cl)(Cl)Cl>CC(C)=O>[I:35][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19]([C:21]1[CH:22]=[N:23][C:24]([N:27]2[CH2:32][CH2:31][N:30]([CH2:33][CH3:34])[CH2:29][CH2:28]2)=[CH:25][CH:26]=1)=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 6212ChloroformHCID 15462632N-(12-mesyloxydodecyl)-6-(4-ethyl-1-piperazinyl)pyridine-3-carboxamide

Product 1

HCID 15462630N-(12-Iodododecyl)-6-(4-ethyl-1-piperazinyl)pyridine-3-carboxamideYield 90.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 72 mg of N-(12-mesyloxydodecyl)-6-(4-ethyl-1-piperazinyl)pyridine-3-carboxamide in acetone was added 130 mg of sodium iodide and the mixture was heated under reflux for 10 hours. To the reaction solution were added water and chloroform and extracted with chloroform. The chloroform layer was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate. The solvent was then distilled off under reduced pressure. The residue thus obtained was chromatographed over a silica gel column to afford 69.0 mg of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 10 hours
  3. extractionextracted with chloroform
  4. washThe chloroform layer was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was then distilled off under reduced pressure
  7. customThe residue thus obtained
  8. customwas chromatographed over a silica gel column

Sources & evidence

ORD record
ord-bd70a45fadf14a3e88374aece715b82e
Source dataset
uspto-grants-2000_04
Patent number
US06046201

Reaction notes

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