Piperidine → 3-Nitro-4-(piperidin-1-yl)aniline

HRID 646850Notes

Reaction equation

HRID 646850 reaction equation
F[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[NH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>C(#N)C>[N+:9]([C:3]1[CH:4]=[C:5]([NH2:6])[CH:7]=[CH:8][C:2]=1[N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 677684-Fluoro-3-nitroaniline

Product 1

HCID 27602373-Nitro-4-(piperidin-1-yl)anilineYield 99%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1.00 g (6.41 mmol) of 4-fluoro-3-nitroaniline and 3.17 mL (32.1 mmol) of piperidine in 15 mL of acetonitrile under Ar was heated to reflux for 2 h. The mixture was cooled to RT, concentrated in vacuo, dissolved in EtOAc (60 mL) and washed with 1 M NaOH (2×50 mL), water (50 mL), brine (50 mL), and then dried (Na2SO4). Concentration afforded 1.40 g (99%) of the title compound as dark red crystals: 1H-NMR (CDCl3; 400 MHz): δ 7.04 (d, 1H, J=8.6 Hz), 7.03 (d, 1H, J=2.8 Hz), 6.81 (dd, 1H, J=8.6, 2.8 Hz), 2.85-2.88 (m, 4H), 1.65-1.70 (m, 4H), and 1.51-1.55 (m, 2H).

Workup

  1. temperatureto reflux for 2 h
  2. concentrationconcentrated in vacuo
  3. dissolutiondissolved in EtOAc (60 mL)
  4. washwashed with 1 M NaOH (2×50 mL), water (50 mL), brine (50 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationConcentration

Sources & evidence

ORD record
ord-6877ec14dc1448b884de8c46bc99ef83
Source dataset
uspto-grants-2010_04
Patent number
US07705042B2

Reaction notes

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