Piperidinium acetate → HCID 178517973, compound

HRID 1620678Notes

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.[CH:24]1([NH:30][C:31]2[CH2:35][S:34][C:33](=[O:36])[N:32]=2)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]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:35]2/[C:31]([NH:30][CH:24]3[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]3)=[N:32][C:33](=[O:36])[S:34]/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 (673 mg) in 2-propanol (15 mL) were added 4-(cyclohexylamino)thiazol-2(5H)-one (590 mg) and piperidinium acetate (294 mg). The reaction mixture was stirred at 80° C. overnight, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) and silica gel column chromatography (NH, methanol/ethyl acetate) to give the title compound (582 mg).

Workup

customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane) and silica gel column chromatography (NH, methanol/ethyl acetate)

Sources & evidence

ORD record: ord-cb6e2ffdcf5b4dfba52b251301135c1b
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772277B2

Reaction notes

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