Piperidine → 4-Chloro-5,7-difluoro-3-methyl-2-(piperidin-1-yl)quinoline

HRID 1618575Notes

Reaction equation

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

Participants

Conditions

Temperature: 85 °C

Procedure

The 2,4-dichloro-5,7-difluoro-3-methylquinoline (300 mg, 1.21 mmol) was dissolved in isopropanol (3 mL) and piperidine (0.120 mL, 1.21 mmol) was added to the sealed tube. The mixture was heated to 85° C. and stirred overnight. The reaction was then cooled and concentrated to dryness. The residue was then purified by medium pressure chromatography (silica, 0 to 40% DCM:hexane) to give 4-chloro-5,7-difluoro-3-methyl-2-(piperidin-1-yl)quinoline. Mass Spectrum (ESI) m/e=297.1 (M+1).

Workup

temperatureThe reaction was then cooled
concentrationconcentrated to dryness
customThe residue was then purified by medium pressure chromatography (silica, 0 to 40% DCM:hexane)

Sources & evidence

ORD record: ord-2343679c411c4aacbc9992abc0a16ece
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765940B2

Reaction notes

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