Piperazine → 2-Methyl-4-(piperazin-1-yl)quinoline

HRID 333947

Reaction equation

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

Participants

Conditions

Temperature: 140 °C

Procedure

4-Chloro-2-methylquinoline (1.8 g, 10 mmol) and anhydrous piperazine (5.25 g, 60 mmol) were dissolved in ethyleneglycol monoethylether (15 ml) and stirred at 140° C. overnight. The mixture was concentrated under reduced pressure, toluene was added (2×100 ml) and the solvent removed under reduced pressure. To the residue was added 0.5 M NaOH (100 ml) and the mixture was extracted with a mixture of dichloromethane/diethylether/ethyl acetate (1:1:1, 3×100 ml). The combined organic phases were washed with brine, dried over sodium sulfate and the solvent was removed under reduced pressure. 2.78 g of an off-white solid (8.5 mmol, 85%) were obtained that were used directly in the next step.

Workup

concentrationThe mixture was concentrated under reduced pressure, toluene
additionwas added (2×100 ml)
customthe solvent removed under reduced pressure
additionTo the residue was added 0.5 M NaOH (100 ml)
extractionthe mixture was extracted with a mixture of dichloromethane/diethylether/ethyl acetate (1:1:1, 3×100 ml)
washThe combined organic phases were washed with brine
dry with materialdried over sodium sulfate
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-c1581ae54b9d4b08ba0367fd12948db5
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883791B2

Linked notes

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