Potassium Carbonate → HCID 86694470, compound

HRID 1519571Notes

Reaction equation

HRID 1519571 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH:2]1[CH2:7][C:8]([O:10][CH3:11])=[O:9].Br[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH3:11][O:10][C:8](=[O:9])[CH2:7][CH:2]1[CH2:3][N:4]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)[CH2:5][CH2:6][N:1]1[CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([N+:21]([O-:23])=[O:22])=[CH:19][CH:20]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 792664-Nitrophenethyl bromideHCID 2774023methyl piperazin-2-ylacetate

Product 1

HCID 86694470HCID 86694470, compound

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of methyl piperazin-2-ylacetate (0.40 g, 1.73 mmol) in DMF (2.5 mL) was added 1-(2-bromoethyl)-4-nitrobenzene (1.0 g, 4.3 mmol), tetrabutyl ammonium iodide (cat.) and potassium carbonate (1.20 g, 8.7 mmol). The mixture was stirred at room temperature for 12 hours. The reaction mixture was diluted with water and extracted with ethyl acetate (3×). The combined organics were washed with water (2×) and brine, then dried (Na2SO4), filtered and concentrated. The desired methyl {1,4-bis[2-(4-nitrophenyl)ethyl]piperazin-2-yl}acetate was purified by mass-directed HPLC. LC-MS (IE, m/z): 456.2 [M+1]+. (0.39 μM)

Workup

  1. extractionextracted with ethyl acetate (3×)
  2. washThe combined organics were washed with water (2×) and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe desired methyl {1,4-bis[2-(4-nitrophenyl)ethyl]piperazin-2-yl}acetate was purified by mass-directed HPLC

Sources & evidence

ORD record
ord-b39c61c363664810ba9011aa5b38638e
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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