Water → HCID 86684783, compound

HRID 330790Notes

Reaction equation

HRID 330790 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:7]=1[Cl:15].[C:16]1([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Cl:15][C:7]1[CH:8]=[CH:9][C:10]([N+:12]([O-:14])=[O:13])=[CH:11][C:6]=1[O:5][CH2:4][CH2:3][CH2:2][N:25]1[CH2:26][CH2:27][N:22]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:23][CH2:24]1

Participants

6

Reactant 4

HCID 962WaterHCID 70961-PhenylpiperazineHCID 11430Potassium CarbonateHCID 3099122-(3-bromopropoxy)-1-chloro-4-nitrobenzene

Product 1

HCID 86684783HCID 86684783, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the compound 26a (2.1 g, 7.1 mmol) in DMF (9 mL) was added N-phenyl piperazine (1.16 g, 7.1 mmol) and potassium carbonate (1.28 g, 9.23 mmol). The mixture was stirred for 18 hrs. at room temperature. Water (10 mL) was added to the reaction mixture and extracted with ethyl acetate (3×20 mL). The combined extracts were dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by flash column chromatography to get the title compound 26b in 78% yield as yellow solid.

Workup

  1. customat room temperature
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. dry with materialThe combined extracts were dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-0b51cb84d1bd4441a423c8fd687574cc
Source dataset
uspto-grants-2014_11
Patent number
US08877752B2

Reaction notes

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