Tetrahydrofuran → HCID 9802919, compound

HRID 459855Notes

Reaction equation

HRID 459855 reaction equation
C1COCC1.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([C:16]2[N:21]=[C:20]([C:22]([OH:24])=O)[CH:19]=[CH:18][CH:17]=2)[CH:11]=[CH:12][C:13]=1[O:14][CH3:15].C(Cl)(=O)C(Cl)=O.[CH3:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([N:39]2[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)=[CH:35][CH:34]=1>CN(C=O)C.O.N1C=CC=CC=1>[CH3:6][O:7][C:8]1[CH:9]=[C:10]([C:16]2[N:21]=[C:20]([C:22]([N:42]3[CH2:41][CH2:40][N:39]([C:36]4[CH:35]=[CH:34][C:33]([O:32][CH3:31])=[CH:38][CH:37]=4)[CH2:44][CH2:43]3)=[O:24])[CH:19]=[CH:18][CH:17]=2)[CH:11]=[CH:12][C:13]=1[O:14][CH3:15]

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 65578Oxalyl chlorideHCID 2697221-(4-Methoxyphenyl)piperazineHCID 220219686-(3,4-Dimethoxyphenyl)pyridine-2-carboxylic acid

Product 1

HCID 9802919HCID 9802919, compoundYield 44.4%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To a THF (20 ml) solution of 500 mg of 6-(3,4-dimethoxyphenyl)pyridine-2-carboxylic acid were added 0.18 ml of oxalyl chloride and one drop of DMF under ice cooling. After 30 minutes ofstirring, the reaction solution was added dropwise to a pyridine (10 ml) solution of 370 mg of 4-(4-methoxyphenyl)piperazine under ice cooling. The mixture was warmed to room temperature and further stirred for 30 minutes. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, and then the solvent was evaporated. The residue was purified by silica gel column chromatography (chloroform-methanol) and recrystallization was further carried out from ethyl acetate-acetonitrile to obtain 370 mg of 1-[6-(3,4-dimethoxyphenyl)pyridine-2-carbonyl]-4-(4-methoxyphenyl)piperazine as colorless crystals.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customThe residue was purified by silica gel column chromatography (chloroform-methanol) and recrystallization

Sources & evidence

ORD record
ord-14ffc634062a4d67bd61f7b46d46741d
Source dataset
uspto-grants-2007_03
Patent number
US07196080B2

Reaction notes

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