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

HRID 2373654Notes

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-3a92dafc4ccf4e2a94979ee51d607c22
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07459456B2

Reaction notes

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