Piperidinium acetate → HCID 86678891, compound

HRID 1620730Notes

Reaction equation

[CH3:1][N:2]([CH3:16])[C:3](=[O:15])[C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9]1[CH2:13][S:12][C:11](=[O:14])[N:10]=1.[F:17][C:18]([F:39])([F:38])[C:19]1[CH:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[CH:30][C:20]=1[CH2:21][N:22]1[CH2:27][CH2:26][CH:25]([CH:28]=O)[CH2:24][CH2:23]1.C([O-])(=O)C.[NH2+]1CCCCC1>CC(O)C>[F:39][C:18]([F:17])([F:38])[C:19]1[CH:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[CH:30][C:20]=1[CH2:21][N:22]1[CH2:27][CH2:26][CH:25](/[CH:28]=[C:13]2/[C:9]([N:5]3[CH2:6][CH2:7][CH2:8][C@H:4]3[C:3]([N:2]([CH3:16])[CH3:1])=[O:15])=[N:10][C:11](=[O:14])[S:12]/2)[CH2:24][CH2:23]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of N,N-dimethyl-1-(2-oxo-2,5-dihydro-1,3-thiazol-4-yl)-L-prolinamide (724 mg) and 1-[2,4-bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde (1018 mg) in 2-propanol (10 mL) was added piperidinium acetate (436 mg) at room temperature. The reaction mixture was stirred at 60° C. overnight, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) and recrystallized from ethyl acetate/heptane to give the title compound (389 mg).

Workup

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

Sources & evidence

ORD record: ord-f7eae12e997d4650872f07b5752c4672
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772277B2

Reaction notes

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