Ethanol → 2-(3-Fluoro-piperidin-1-yl)-4-(4-methyl-piperazin-1-yl)-phenylamine

HRID 646951Notes

Reaction equation

[F:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([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)[CH2:3]1.CCO.O>CC(O)=O.CCOC(C)=O.[Fe]>[F:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([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])[CH2:3]1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 1-[3-(3-fluoro-piperidin-1-yl)-4-nitro-phenyl]4-methyl-piperazine (as prepared in the previous step, 60 mg, 0.19 mmol) in 2:1 EtOH:water (6 mL), was treated with glacial AcOH (1 drop) and iron powder (10 mg, 0.93 mmol). The mixture was heated to 80° C. for 30 min. The reaction cooled to room temperature, diluted with EtOAc and washed with saturated aqueous NaHCO3. The aqueous layer was extracted with EtOAc. The combined organic layers were dried over MgSO4 and concentrated in vacuo to afford the title compound (46 mg, 84%), which was used directly in the next reaction. LC-MS (ESI, m/z): Calcd. for C16H25FN4 293.2 (M+H), found 293.2.

Workup

temperatureThe reaction cooled to room temperature
washwashed with saturated aqueous NaHCO3
extractionThe aqueous layer was extracted with EtOAc
dry with materialThe combined organic layers were dried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-62bbcfd1fb90486297a54018465ed8b9
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07705042B2

Reaction notes

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