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

HRID 419467Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[C:7](F)[CH:6]=[CH:5][C:4]=1[N+:10]([O-:12])=[O:11].[NH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH:6]=[CH:5][C:4]=1[N+:10]([O-:12])=[O:11]

Participants

Conditions

Temperature: 120 °C

Procedure

To 5-fluoro-2-nitrophenyl methyl ether (Example 22, step A) (0.8 g, 4.67 mmol) in 10 mL of dioxane was added, piperazine (1.2 g, 14 mmol). The mixture was heated to 120° C. for 2 h. The mixture was purified by flash chromatography to give the title compound of step A (1 g, 4.2 mmol, 90%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.85 (d, J=9.34 Hz, 1H), 6.55 (d, J=2.56 Hz, 1H), 6.52 (s, 1H), 6.46 (d, J=2.56 Hz, 1H), 3.87 (s, 3H), 3.25-3.33 (m, 4H), 2.73-2.79 (m, 4H).

Workup

customThe mixture was purified by flash chromatography

Sources & evidence

ORD record: ord-3c2921f2e5a54ae28bee6eb29895b5b5
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093239B2

Reaction notes

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