Piperazine → 1-(3-Ethoxy-4-nitrophenyl)piperazine

HRID 419488

Reaction equation

HRID 419488 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[C:8](F)[CH:7]=[CH:6][C:5]=1[N+:11]([O-:13])=[O:12])[CH3:2].[NH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1>O1CCOCC1>[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[CH:7]=[CH:6][C:5]=1[N+:11]([O-:13])=[O:12])[CH3:2]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 129181532-Ethoxy-4-fluoronitrobenzene

Product 1

HCID 594525801-(3-Ethoxy-4-nitrophenyl)piperazineYield 88.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

To 2-(ethyloxy)-4-fluoro-1-nitrobenzene (Example 116, step A) (3.0 g, 16.2 mmol) in 60 mL of dioxane was added, piperazine (4.19 g, 48.61 mmol). The mixture was heated to 120° C. 72 h. The mixture was purified by flash chromatography to give the title compound of step A (3.6 g, 14.33 mmol, 88%). 1H NMR (400 MHz, CDCl3) δ ppm 7.95 (d, J=9.34 Hz, 1H), 6.40 (dd, J=9.34, 2.56 Hz, 1H), 6.30 (d, J=2.56 Hz, 1H), 4.13 (q, J=6.96 Hz, 2H), 3.30-3.33 (m, 4H), 2.95-3.02 (m, 4H), 1.48 (t, J=6.96 Hz, 3H).

Workup

  1. custom72 h
  2. customThe mixture was purified by flash chromatography

Sources & evidence

ORD record
ord-2ec0442dfb1b43c096f9eb553be59801
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Linked notes

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