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

HRID 640982

Reaction equation

HRID 640982 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 (3×30 mL), and with brine (2×30 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 (3×30 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-c486cb75037c446daf6a0ce5de609333
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Linked notes

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