Dimethyl Sulfoxide → 7-Fluoro-2-methyl-5-piperazin-1-ylquinoline

HRID 1179635Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Cl.F[C:15]1[CH:24]=[C:23]([F:25])[CH:22]=[C:21]2[C:16]=1[CH:17]=[CH:18][C:19]([CH3:26])=[N:20]2.CS(C)=O>O>[CH3:26][C:19]1[CH:18]=[CH:17][C:16]2[C:21](=[CH:22][C:23]([F:25])=[CH:24][C:15]=2[N:1]2[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)[N:20]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A stirred mixture of piperazine (20 g), potassium carbonate (32 g), 5,7-difluoro-2-methylquinoline hydrochloride (WO2002034754, 20 g) and dimethylsulfoxide (390 mL) was heated to 120° C. for 15 hours. The mixture was cooled to room temperature, diluted with water (600 mL) and extracted with 6×500 mL portions of a mixture of DCM-ether (15:85). The combined organic extracts were washed with water (200 mL) and brine (200 mL), dried (sodium sulfate) and the solvent was partially evaporated under vacuum. The precipitate formed during the evaporation was filtered-off, washed with ether (50 mL) and dried under vacuum to give the title compound (4.7 g, 21%).

Workup

temperatureThe mixture was cooled to room temperature
extractionextracted with 6×500 mL portions of a mixture of DCM-ether (15:85)
washThe combined organic extracts were washed with water (200 mL) and brine (200 mL)
dry with materialdried (sodium sulfate)
customthe solvent was partially evaporated under vacuum
customThe precipitate formed during the evaporation
washwashed with ether (50 mL)
customdried under vacuum

Sources & evidence

ORD record: ord-a363517874be4b7e955654e08c260b2a
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07279481B2

Reaction notes

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