1-Methylpiperazine → 3-(4-Fluoro-piperidin-1-yl)-4-nitro-phenyl-4-methyl-piperazine

HRID 646947Notes

Reaction equation

Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:15]([O-:17])=[O:16])=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([F:14])[CH2:10][CH2:9]2)[CH:7]=1.[CH3:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>C(Cl)Cl>[F:14][CH:11]1[CH2:12][CH2:13][N:8]([C:6]2[CH:7]=[C:2]([N:22]3[CH2:23][CH2:24][N:19]([CH3:18])[CH2:20][CH2:21]3)[CH:3]=[CH:4][C:5]=2[N+:15]([O-:17])=[O:16])[CH2:9][CH2:10]1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 1-(5-chloro-2-nitro-phenyl)-4-fluoro-piperidine (as prepared in the previous step, 0.44 g, 1.7 mmol) in 4-methylpiperazine (2 mL) was heated to 80° C. for 18.5 h. The solution was cooled to room temperature, diluted with CH2Cl2, and washed with water. The aqueous layer was further extracted with CH2Cl2. The combined organic layers were dried over MgSO4 and concentrated in vacuo to afford the title compound (0.51 g, 93%) as a bright yellow solid. 1H-NMR (CDCl3; 400 MHz): δ 8.04 (d, 1H, J=9.2 Hz), 6.45 (dd, 1H, J=9.2 Hz, J=2.4 Hz), 6.34 (d, 1H, J=2.4 Hz), 4.97-4.79 (m, 1H), 3.38 (app t, 4H, J=5.2 Hz), 3.26-3.15 (m, 4H), 3.07-2.98 (m, 4H), 2.54 (app t, 4H, J=5.2 Hz), 2.35 (s, 3H). LC-MS (ESI, m/z): Calcd. for C16H23FN4O2, 323.2 (M+H), found 323.2.

Workup

temperatureThe solution was cooled to room temperature
washwashed with water
extractionThe aqueous layer was further extracted with CH2Cl2
dry with materialThe combined organic layers were dried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-a45aa67b0f8f4a6f9e08f351eb8c6b6e
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07705042B2

Reaction notes

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