Water → HCID 22318639, compound

HRID 497328Notes

Reaction equation

HRID 497328 reaction equation
Cl.Cl.Cl.Cl.[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([N:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)[CH2:13][N:14]2[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][CH2:22][CH2:23][C:24]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:27]=[CH:26][CH:25]=3)[CH2:16][CH2:15]2)=[CH:8][CH:7]=1.[H-].[Na+].Br[CH:43]([CH3:45])[CH3:44].O>CN(C)C=O>[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([N:34]2[CH2:39][CH2:38][N:37]([CH:43]([CH3:45])[CH3:44])[CH2:36][CH2:35]2)[CH2:13][N:14]2[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][CH2:22][CH2:23][C:24]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:27]=[CH:26][CH:25]=3)[CH2:16][CH2:15]2)=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 63582-BromopropaneHCID 24758Sodium hydrideHCID 22318656HCID 22318656, compound

Product 1

HCID 22318639HCID 22318639, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

0.2 g of 1-[2-(4-Fluorophenyl)-2-piperazinoethyl]-4-(4-naphthalen-1-yl-butyl)piperazine tetrahydrochloride was dissolved in 0.7 ml of dimethylformamide, and 74 mg of 60% sodium hydride in oil was added with ice-cooling. The temperature was elevated to room temperature, followed by stirring for 10 minutes. To the reaction solution was added a 0.3 ml of dimethylformamide solution of 0.2 g of 2-bromopropane, followed by stirring overnight. The reaction solution was poured to water and, after extraction with ethyl acetate, the organic layer was washed with a saturated aqueous sodium chloride solution and 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 (Chromatorex NH, hexane:ethyl acetate=1:1) to give 0.13 g of 1-[2-(4-fluorophenyl)-2-(4-isopropylpiperazino)ethyl]-4-(4-naphthalen-1-yl-butyl)piperazine as an oil.

Workup

  1. temperaturecooling
  2. customwas elevated to room temperature
  3. stirringby stirring overnight
  4. extractionafter extraction with ethyl acetate
  5. washthe organic layer was washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. customAfter removal of the drying agent
  8. filtrationby filtration
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customthe residue was purified by a silica gel column chromatography (Chromatorex NH, hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-a25c1cee27ee490f997d372fbbfde633
Source dataset
uspto-grants-2005_09
Patent number
US06949552B2

Reaction notes

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