Piperidinium acetate → HCID 178463637, compound

HRID 1620780Notes

Reaction equation

[CH2:1]([NH:3][C:4]1[CH2:8][S:7][C:6](=[O:9])[N:5]=1)[CH3:2].[F:10][C:11]([F:32])([F:31])[C:12]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[CH:23][C:13]=1[CH2:14][N:15]1[CH2:20][CH2:19][CH:18]([CH:21]=O)[CH2:17][CH2:16]1.C([O-])(=O)C.[NH2+]1CCCCC1>CC(O)C>[F:32][C:11]([F:10])([F:31])[C:12]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[CH:23][C:13]=1[CH2:14][N:15]1[CH2:20][CH2:19][CH:18](/[CH:21]=[C:8]2/[C:4]([NH:3][CH2:1][CH3:2])=[N:5][C:6](=[O:9])[S:7]/2)[CH2:17][CH2:16]1

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of 4-(ethylamino)-1,3-thiazol-2(5H)-one (310 mg) and 1-[2,4-bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde (802 mg) in 2-propanol (10 mL) was added piperidinium acetate (312 mg). The reaction mixture was stirred at 75° C. for 4 hr and concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane), and the obtained solid was washed with diisopropyl ether to give the title compound (110 mg).

Workup

concentrationconcentrated under reduced pressure
additionWater was added to the residue
extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
washthe obtained solid was washed with diisopropyl ether

Sources & evidence

ORD record: ord-dd80c8d118f84dbe82874d58cc0598b7
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772277B2

Reaction notes

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