Sodium Bicarbonate → HCID 22318672, compound

HRID 497325Notes

Reaction equation

HRID 497325 reaction equation
[C:1]1([CH2:11][CH2:12][CH2:13][C:14](Cl)=[O:15])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[F:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]([N:32]2[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]2)[CH2:25][N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:20][CH:19]=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[F:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]([N:32]2[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]2)[CH2:25][N:26]2[CH2:31][CH2:30][N:29]([C:14](=[O:15])[CH2:13][CH2:12][CH2:11][C:1]3[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH:4]=[CH:3][CH:2]=3)[CH2:28][CH2:27]2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 10957750Piperazine, 1-[1-(4-fluorophenyl)-2-(1-piperazinyl)ethyl]-4-methyl-HCID 22318647HCID 22318647, compound

Product 1

HCID 22318672HCID 22318672, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.37 g of 4-Naphthalen-1-yl-butyric acid was dissolved in 5.0 ml of toluene, and 0.35 ml of thionyl chloride and 1 drop of dimethylformamide were added, followed by heating at 70° C. for 30 minutes. The reaction solution was cooled to room temperature and concentrated under reduced pressure to give a crude 4-naphthalen-1-yl-butyryl chloride. To the resulting crude 4-naphthalen-1-yl-butyryl chloride was added 2.3 ml of a toluene solution of 0.40 g of 1-[2-(4-fluorophenyl)-2-(4-methylpiperazino)ethyl]piperazine, followed by stirring at room temperature for 30 minutes. To the reaction solution was added a saturated aqueous sodium bicarbonate solution and, after extraction with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by a silica gel column chromatography (Wako-gel C-200, chloroform:methanol=10:1) to give 0.58 g of 1-[2-(4-fluorophenyl)-2-(4-methylpiperazino)ethyl]-4-(4-naphthalen-1-yl-butyryl)piperazine as an oil.

Workup

  1. extractionafter extraction with ethyl acetate
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. customAfter removal of the drying agent
  4. filtrationby filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by a silica gel column chromatography (Wako-gel C-200, chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-002898ce7fe6459e8f1ed5e8f1e1c018
Source dataset
uspto-grants-2005_09
Patent number
US06949552B2

Reaction notes

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