Piperidinium acetate → HCID 178518111, compound

HRID 1620622Notes

Reaction equation

[F:1][C:2]([F:23])([F:22])[C:3]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([CH:12]=O)[CH2:8][CH2:7]1.[OH:24][CH2:25][C:26]1([CH2:32][NH:33][C:34]2[CH2:38][S:37][C:36](=[O:39])[N:35]=2)[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.C([O-])(=O)C.[NH2+]1CCCCC1>CC(O)C>[F:23][C:2]([F:1])([F:22])[C:3]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][CH:9](/[CH:12]=[C:38]2/[C:34]([NH:33][CH2:32][C:26]3([CH2:25][OH:24])[CH2:27][CH2:28][O:29][CH2:30][CH2:31]3)=[N:35][C:36](=[O:39])[S:37]/2)[CH2:8][CH2:7]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1-[2,4-bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde (972 mg) in 2-propanol (20 mL) were added 4-({[4-(hydroxymethyl)tetrahydro-2H-pyran-4-yl]methyl}amino)thiazol-2(5H)-one (1.05 g) and piperidinium acetate (425 mg). The reaction mixture was stirred at 80° C. overnight and concentrated 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 (774 mg).

Workup

concentrationconcentrated 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-c8f6cd110abf44f5abf9ad5e69ffe3d6
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772277B2

Reaction notes

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