Ethanol → 2-(4-Fluoro-piperidin-1-yl)-4-(4-methyl-piperazin-1-yl)-phenylamine

HRID 646948Notes

Reaction equation

[F:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[C:10]([N:17]3[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]3)[CH:11]=[CH:12][C:13]=2[N+:14]([O-])=O)[CH2:4][CH2:3]1.CCO.[NH4+].[Cl-].C([O-])(O)=O.[Na+]>C(O)(=O)C.[Fe].O>[F:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[C:10]([N:17]3[CH2:18][CH2:19][N:20]([CH3:23])[CH2:21][CH2:22]3)[CH:11]=[CH:12][C:13]=2[NH2:14])[CH2:4][CH2:3]1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 1-[3-(4-fluoro-piperidin-1-yl)-4-nitro-phenyl]-4-methyl-piperazine (as prepared in the previous step, 0.20 g, 0.62 mmol) in 2:1 EtOH:water (6 mL) was treated with solid NH4Cl (0.33 g, 6.2 mmol) and iron powder (0.17 g, 3.1 mmol) then heated to 100° C. for 2.5 h. The reaction was cooled to room temperature, treated with 1 drop of glacial acetic acid, and heated again to 100° C. for 30 min. The reaction was cooled to room temperature and neutralized with saturated aqueous NaHCO3. The product was extracted with CH2Cl2, and the combined organic layers were dried over MgSO4 and concentrated in vacuo to afford the title compound (0.19 g, 99%), which was used immediately in the next reaction. LC-MS (ESI, m/z): Calcd. for C16H25FN4, 293.2 (M+H), found 293.1.

Workup

temperatureThe reaction was cooled to room temperature
temperatureheated again to 100° C. for 30 min
extractionThe product was extracted with CH2Cl2
dry with materialthe combined organic layers were dried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-8f5b3e8887be4a0f85fd810395f7c5e6
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07705042B2

Reaction notes

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