1-Methylpiperazine → 3-(4-Methylpiperazin-1-yl)-2-nitroaniline

HRID 470342Notes

Reaction equation

HRID 470342 reaction equation
Cl[C:2]1[C:3]([N+:9]([O-:11])=[O:10])=[C:4]([NH2:8])[CH:5]=[CH:6][CH:7]=1.[CH3:12][N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1>>[CH3:12][N:13]1[CH2:18][CH2:17][N:16]([C:2]2[C:3]([N+:9]([O-:11])=[O:10])=[C:4]([NH2:8])[CH:5]=[CH:6][CH:7]=2)[CH2:15][CH2:14]1

Participants

3

Reactant 2

HCID 531671-MethylpiperazineHCID 1010683-Chloro-2-nitroaniline

Product 1

HCID 461799823-(4-Methylpiperazin-1-yl)-2-nitroanilineYield 59%

Procedure

A mixture of 3-chloro-2-nitro-phenylamine (172.6 mg, 1 mmol) and 1-methyl-piperazine (1.5 mL) was heated at 200° C. in a Biotage Initiator Sixty microwave reactor for 15 min, cooled to the room temperature, and concentrated under reduced pressure. The residue was purified by chromatography (500:10:1 CH2Cl2/MeOH/28% aqueous NH4OH) to afford the title compound (139 mg, 59%). 1H NMR (MeOH-d4) δ 2.32 (s, 3H), 2.55 (m, 4H), 2.99 (m, 4H), 6.45 (d, J=9 Hz, 1H), 6.57 (d, J=9 Hz, 1H), 7.15 (dd, J=9 Hz and 9 Hz, 1H). ESI-MS m/z 237.3 (MH+).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by chromatography (500:10:1 CH2Cl2/MeOH/28% aqueous NH4OH)

Sources & evidence

ORD record
ord-0586d3ba7bc9489db56c80fa9b58414a
Source dataset
uspto-grants-2014_01
Patent number
US08629147B2

Reaction notes

Loading…