Piperazine → 2-Methyl-4-piperazin-1-yl-7-(trifluoromethyl)quinoline

HRID 333958

Reaction equation

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

Participants

Conditions

Temperature: 140 °C

Procedure

2-Methyl-4-chloro-7-(trifluoromethyl)quinoline (1.1 g, 4.4 mmol) was dissolved in dipropyleneglycolmonomethylether, piperazine was added (12 g, 14 mmol) and the mixture was stirred at 140° C. overnight. The solvent was removed under reduced pressure and the residue purified by column chromatography (prepacked silica column, gradient ethyl acetate/methanol with the addition of 1% ammonia) to yield 1.07 g of a solid. (3.6 mmol, 82%) MS (APCI): m/z=295.8 [M+1]+.

Workup

customThe solvent was removed under reduced pressure
customthe residue purified by column chromatography (prepacked silica column, gradient ethyl acetate/methanol
additionwith the addition of 1% ammonia)

Sources & evidence

ORD record: ord-374e4806ed4545ceb827d566c07fdfb5
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883791B2

Linked notes

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