1-Methylpiperazine → 1-Methyl-4-{3-[3-(methyloxy)-4-nitrophenyl]-2-propyn-1-yl}piperazine

HRID 419484Notes

Reaction equation

Cl[CH2:2][C:3]#[C:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[C:7]([O:14][CH3:15])[CH:6]=1.[CH3:16][N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1>O1CCOCC1>[CH3:16][N:17]1[CH2:22][CH2:21][N:20]([CH2:2][C:3]#[C:4][C:5]2[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[C:7]([O:14][CH3:15])[CH:6]=2)[CH2:19][CH2:18]1

Participants

Conditions

Temperature: 110 °C

Procedure

To 4-(3-chloro-1-propyn-1-yl)-2-(methyloxy)-1-nitrobenzene (Example 139, step B) (0.250 g, 1.1 mmol) in 10 mL of dioxane was added, 1-methylpiperazine (0.31 g, 3.1 mmol). The mixture was heated to 110° C. for 3 h. The mixture was purified by flash chromatography to give the title compound of step A (0.309 g, 1.07 mmol, 97%). 1H NMR (400 MHz, CDCl3) δ ppm 7.78 (d, J=8.24 Hz, 1H), 7.11 (s, 1H), 7.04 (dd, J=8.33, 1.56 Hz, 1H), 3.94 (s, 3H), 3.55 (s, 2H), 2.64-2.78 (m, 4H), 2.47-2.62 (m, 4H), 2.33 (s, 3H).

Workup

customThe mixture was purified by flash chromatography

Sources & evidence

ORD record: ord-95999df0284841d3b3267bc7c4e7fb08
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093239B2

Reaction notes

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