1-Methylpiperazine → 1-Methyl-4-{2-[3-(ethyloxy)-4-nitrophenyl]ethyl}piperazine

HRID 419496Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([CH:10]=[CH2:11])[CH:7]=[CH:6][C:5]=1[N+:12]([O-:14])=[O:13])[CH3:2].[CH3:15][N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1>CC(O)C>[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([CH2:10][CH2:11][N:19]2[CH2:20][CH2:21][N:16]([CH3:15])[CH2:17][CH2:18]2)[CH:7]=[CH:6][C:5]=1[N+:12]([O-:14])=[O:13])[CH3:2]

Participants

Conditions

Temperature: 120 °C

Procedure

To 5-ethenyl-2-nitrophenyl ethyl ether (0.53 g, 2.74 mmol) in 10 mL of iPrOH was added, 1-methylpiperazine (0.41 g, 4.11 mmol). The mixture was heated to 120° C. for 2 h. The solvent was rotovaped down and the crude product was purified by flash chromatography to give the title compound of step C (0.708 g, 2.4 mmol, 88%). 1H NMR (400 MHz, CDCl3) δ ppm 7.75 (d, J=8.42 Hz, 1H), 6.90 (d, J=1.47 Hz, 1H), 6.82 (dd, J=8.42, 1.47 Hz, 1H), 4.15 (q, J=6.96 Hz, 2H), 2.78-2.83 (m, 2H), 2.33-2.88 (m, 10H), 2.30 (s, 3H), 1.46 (t, J=6.96 Hz, 3H).

Workup

customthe crude product was purified by flash chromatography

Sources & evidence

ORD record: ord-ea0c620332ed48fe9cd94eea9ec05cbd
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093239B2

Reaction notes

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