5-Fluoro-2-nitroaniline → 5-(4-Ethylpiperazin-1-yl)-2-nitroaniline

HRID 58167

Reaction equation

HRID 58167 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1)[CH3:2].F[C:10]1[CH:11]=[CH:12][C:13]([N+:17]([O-:19])=[O:18])=[C:14]([NH2:16])[CH:15]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:10]2[CH:11]=[CH:12][C:13]([N+:17]([O-:19])=[O:18])=[C:14]([NH2:16])[CH:15]=2)[CH2:5][CH2:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 753995-Fluoro-2-nitroanilineHCID 791961-EthylpiperazineHCID 81531Diisopropylethylamine

Product 1

HCID 598459045-(4-Ethylpiperazin-1-yl)-2-nitroanilineYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1-ethyl-piperazine (1.2 mL, 9.6 mmol), 5-fluoro-2-nitro-phenylamine (1 g, 6.4 mmol), DIPEA (1.24 g, 9.6 mmol) in DMF (15 mL) was heated at 80° C. overnight. The reaction mixture was poured into ice water and extracted with EtOAc. The combined extract was washed with brine, dried over anhydrous Na2SO4, and concentrated to obtain a crude product, which was purified by flash chromatography on silica to afford the title compound (1 g, yield: 63%). ESI-MS: 251 [M+H]+.

Workup

  1. extractionextracted with EtOAc
  2. extractionThe combined extract
  3. washwas washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customto obtain a crude product, which
  7. customwas purified by flash chromatography on silica

Sources & evidence

ORD record
ord-3f74ea3f2502403bbb775209eb0e19b6
Source dataset
uspto-grants-2016_09
Patent number
US09434697B2

Linked notes

Loading…