Tetrahydrofuran → 1-methyl-4-(2-nitrophenyl)piperazine

HRID 2369109Notes

Reaction equation

HRID 2369109 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[CH3:11][N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C1COCC1>CCOC(C)=O>[CH3:11][N:12]1[CH2:17][CH2:16][N:15]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 531671-MethylpiperazineHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 4106401-methyl-4-(2-nitrophenyl)piperazineYield 97%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a Kontes glass tube was added 2-fluoro-nitrobenzene (3.34 g, 23.7 mmol), 1-methyl-piperazine (3.90 mL, 35.6 mmol), and anhydrous THF (10 mL). The tube was sealed and the reaction mixture was allowed to stir at 60° C. for 1 day. The reaction solution was diluted with EtOAc (150 mL), washed with aq NaHCO3, dried over Na2SO4, filtered, and concentrated in vacuo to afford 5.07 g (97% yield) of the title product. MS (ES) 222.3 [M+H]+.

Workup

  1. customThe tube was sealed
  2. washwashed with aq NaHCO3
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f4bc4aea0497492eac93062e5f08cb1b
Source dataset
uspto-grants-2014_04
Patent number
US08703805B2

Reaction notes

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