Sodium Iodide → HCID 10184800, compound

HRID 459865Notes

Reaction equation

HRID 459865 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]4[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH3:31])[CH:23]=4)[N:17]=3)=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl[CH2:33][CH2:34][O:35][CH2:36][CH2:37]Cl.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:31][O:30][C:24]1[CH:23]=[C:22]([C:18]2[N:17]=[C:16]([C:14]([N:11]3[CH2:10][CH2:9][N:8]([C:5]4[CH:4]=[CH:3][C:2]([N:1]5[CH2:37][CH2:36][O:35][CH2:34][CH2:33]5)=[CH:7][CH:6]=4)[CH2:13][CH2:12]3)=[O:15])[CH:21]=[CH:20][CH:19]=2)[CH:27]=[CH:26][C:25]=1[O:28][CH3:29]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8115Bis(2-chloroethyl) etherHCID 11430Potassium CarbonateHCID 22930977HCID 22930977, compound

Product 1

HCID 10184800HCID 10184800, compoundYield 50.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a DMF (3 ml) solution of 355 mg of 1-(4-aminophenyl)-4-[6-(3,4-dimethoxyphenyl)pyridine-2-carbonyl]piperazine were added 130 mg of 1-chloro-2-(2-chloroethoxy)ethane, 77 mg of sodium iodide and 249 mg of potassium carbonate, followed by overnight stirring at 100° C. After cooled to room temperature, the reaction solution was concentrated under reduced pressure and then water was added thereto, followed by extraction with chloroform. The organic layer was washed with brine and then dried over anhydrous magnesium sulfate, and thereafter, the solvent was evaporated. The residue was purified by silica gel column chromatography (chloroform-methanol) and then crystallization was carried out from ethanol-diethyl ether to obtain 210 mg of 4-(4-{4-[6-(3,4-dimethoxyphenyl)pyridine-2-carbonyl]piperazin-1-yl)phenyl)morpholine as yellow crystals.

Workup

  1. temperatureAfter cooled to room temperature
  2. concentrationthe reaction solution was concentrated under reduced pressure
  3. additionwater was added
  4. extractionfollowed by extraction with chloroform
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated
  8. customThe residue was purified by silica gel column chromatography (chloroform-methanol)
  9. customcrystallization

Sources & evidence

ORD record
ord-6dfa4ead960441c4afe778fdb7e329af
Source dataset
uspto-grants-2007_03
Patent number
US07196080B2

Reaction notes

Loading…