Piperazine → 5-Nitro-2-(piperazin-1-yl)benzenamine

HRID 1966451Notes

Reaction equation

HRID 1966451 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[NH2:11].[NH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1>CN1C(=O)CCC1>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[C:3]([NH2:11])[CH:4]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 677852-Fluoro-5-nitroaniline

Product 1

HCID 584256705-Nitro-2-(piperazin-1-yl)benzenamineYield 70.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 2-fluoro-5-nitrobenzenamine (0.50 g, 3.2 mmol) and piperazine (0.83 g, 9.6 mmol) in 15 ml NMP was heated at 100° C. for 16 hours. The reaction was quenched with 100 ml water. Red solids were filtered and dried under high vacuum. 5-Nitro-2-(piperazin-1-yl)benzenamine (0.50 g, 70%) was obtained by crystallization in acetyl acetate and hexanes. 1H NMR (500 MHz, DMSO-d6) δ (ppm) 2.23 (s, 1H), 2.86 (m, 8H), 5.26 (s, 2H), 6.98 (d, J=8.7 Hz, 1H), 7.45 (dd, J=8.7, 2.8 Hz, 1H), 7.54 (d, J=8.7 Hz, 1H).

Workup

  1. customThe reaction was quenched with 100 ml water
  2. filtrationRed solids were filtered
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-e3c3166092db4f11aa567bf332b21b4a
Source dataset
uspto-grants-2013_04
Patent number
US08420640B2

Reaction notes

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