Diisopropylamine → N-[3-(4-methylpiperazin-1-yl)propyl]-4-nitro-1-aminobenzene

HRID 11557

Reaction equation

HRID 11557 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[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(NC(C)C)(C)C>O1CCOCC1>[CH3:11][N:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH2:20][NH:21][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 9590p-FluoronitrobenzeneHCID 783281-(3-Aminopropyl)-4-methylpiperazine

Product 1

HCID 21975010N-[3-(4-methylpiperazin-1-yl)propyl]-4-nitro-1-aminobenzene

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4.44 mL of p-fluoronitrobenzene, 6 gms. 3-(4-methyl-piperazin-1-yl)-propylamine and 6.65 mL N,N-diisopropylamine in 19 mL dioxane is heated at 105° C. for 2 days. The reaction mixture is cooled to room temperature, evaporated to dryness, and recrystallized from hot isopropanol yielding [3-(4-methyl-piperazin-1-yl)-propyl]-(4-nitro-phenyl)-amine in the amount of 0.1385 gms.

Workup

  1. customevaporated to dryness
  2. customrecrystallized from hot isopropanol

Sources & evidence

ORD record
ord-bd5c83c4a79a42c4a343217e1748191c
Source dataset
uspto-grants-2006_08
Patent number
US07098236B2

Linked notes

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