Piperidinium acetate → HCID 178456896, compound

HRID 1620598Notes

Reaction equation

[CH:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][C:10]=2[C:17]([F:20])([F:19])[F:18])[CH2:5][CH2:4]1)=O.[CH2:21]([NH:24][C:25]1[CH2:29][S:28][C:27](=[O:30])[N:26]=1)[C:22]#[CH:23].C([O-])(=O)C.[NH2+]1CCCCC1>CC(O)C>[O:30]=[C:27]1[N:26]=[C:25]([NH:24][CH2:21][C:22]#[CH:23])/[C:29](=[CH:1]/[CH:3]2[CH2:8][CH2:7][N:6]([C:9]3[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][C:10]=3[C:17]([F:20])([F:19])[F:18])[CH2:5][CH2:4]2)/[S:28]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-(4-formylpiperidin-1-yl)-3-(trifluoromethyl)benzonitrile (800 mg) in 2-propanol (15 mL) were added 4-(prop-2-yn-1-ylamino)-1,3-thiazol-2(5H)-one (874 mg) and piperidinium acetate (420 mg). The reaction mixture was stirred at 60° C. overnight and concentrated. Water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with water and 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 recrystallized from ethyl acetate/heptane to give the title compound (849 mg).

Workup

concentrationconcentrated
additionWater was added to the residue
extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with water and 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)
customrecrystallized from ethyl acetate/heptane

Sources & evidence

ORD record: ord-367e3a45da284b9dab824f95d5db5a14
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772277B2

Reaction notes

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