Dimethylformamide → HCID 18444267, compound

HRID 459862Notes

Reaction equation

HRID 459862 reaction equation
CN(C=O)C.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([C:16]2[N:21]=[C:20]([C:22]([N:24]3[CH2:29][CH2:28][N:27]([C:30]4[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=4)[CH2:26][CH2:25]3)=[O:23])[CH:19]=[CH:18][CH:17]=2)[CH:11]=[CH:12][C:13]=1[O:14][CH3:15].Cl[CH2:38][C:39]1[CH:44]=[CH:43][N+:42]([O-:45])=[CH:41][CH:40]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O>[CH3:6][O:7][C:8]1[CH:9]=[C:10]([C:16]2[N:21]=[C:20]([C:22]([N:24]3[CH2:25][CH2:26][N:27]([C:30]4[CH:31]=[CH:32][C:33]([O:36][CH2:38][C:39]5[CH:44]=[CH:43][N+:42]([O-:45])=[CH:41][CH:40]=5)=[CH:34][CH:35]=4)[CH2:28][CH2:29]3)=[O:23])[CH:19]=[CH:18][CH:17]=2)[CH:11]=[CH:12][C:13]=1[O:14][CH3:15]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonate2×HCID 12487457HCID 12487457, compound2×HCID 18444282HCID 18444282, compound

Product 1

HCID 18444267HCID 18444267, compoundYield 23.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a DMF (10 ml) solution of 1.50 g of 4-{4-[6-(3,4-dimethoxyphenyl)pyridine-2-carbonyl]piperazin-1-yl}phenol were added 1.00 g of 4-chloromethylpyridine-N-oxide and 3.00 g of cesium carbonate, followed by 30 minutes of stirring at room temperature. After warmed to 60° C., the mixture was further stirred for 30 minutes. Then, 1.00 g of 4-chloromethylpyridine-N-oxide and 1.50 g of cesium carbonate were added thereto and the whole was stirred at 60° C. for 1 hour. After cooling to room temperature, water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with water and 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 recrystallization was carried out from ethanol to obtain 440 mg of 1-[6-(3,4-dimethoxyphenyl)pyridine-2-carbonyl]-4-[4-(1-oxido-4-pyridylmethoxy)phenyl]piperazine as pale yellow crystals.

Workup

  1. temperatureAfter warmed to 60° C.
  2. stirringthe mixture was further stirred for 30 minutes
  3. stirringthe whole was stirred at 60° C. for 1 hour
  4. temperatureAfter cooling to room temperature
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with water and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated
  9. customThe residue was purified by silica gel column chromatography (chloroform-methanol)
  10. customrecrystallization

Sources & evidence

ORD record
ord-0b1bc1c5a694430896240f1afaac6295
Source dataset
uspto-grants-2007_03
Patent number
US07196080B2

Reaction notes

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