1-Fluoro-2-nitrobenzene → N-[3-(4-methylpiperazin-1-yl)propyl]-4-nitro-1-aminobenzene

HRID 2352914Notes

Reaction equation

HRID 2352914 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][N:15]([CH2:18][CH2:19][CH2:20][NH2:21])[CH2:14][CH2:13]1.C(N(C(C)C)CC)(C)C>O1CCOCC1>[CH3:11][N:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH2:20][NH:21][C:6]2[CH:5]=[CH:4][C:3]([N+:8]([O-:10])=[O:9])=[CH:2][CH:7]=2)[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 738951-Fluoro-2-nitrobenzeneHCID 783281-(3-Aminopropyl)-4-methylpiperazineHCID 81531Diisopropylethylamine

Product 1

HCID 21975010N-[3-(4-methylpiperazin-1-yl)propyl]-4-nitro-1-aminobenzeneYield 74%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A 100 mL round bottom flask was dried in an oven overnight and cooled to room temperature under Ar(g). The flask was charged with fluoronitrobenzene (0.187 mL, 1.77 mmol), 3-(4-Methyl-piperazin-1-yl)-propylamine (0.361 g, 2.30 mmol) and dioxane (9.0 mL). To the resulting solution diisopropyl ethyl amine (0.463 mL, 2.66 mmol) was added dropwise and allowed to stir at 105° C. for 48 h. The mixture was extracted with EtOAc (3ט30 mL), and with brine (2ט30 mL). The combined organic layers were then dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude mixture was then purified over silica (10% MeOH/90% CHCl3) affording a yellow solid (0.365 g, 1.31 mmol, 74% yield).

Workup

  1. customA 100 mL round bottom flask was dried in an oven overnight
  2. extractionThe mixture was extracted with EtOAc (3ט30 mL)
  3. dry with materialThe combined organic layers were then dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude mixture was then purified over silica (10% MeOH/90% CHCl3)

Sources & evidence

ORD record
ord-e9e2b98fd8824ff4b0b8dec9dd50aa6b
Source dataset
uspto-grants-2010_07
Patent number
US07749530B2

Reaction notes

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