Piperidinium acetate → HCID 178451231, compound

HRID 1620609Notes

Reaction equation

[O:1]=[C:2]1[N:6]=[C:5]([NH:7][CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4][S:3]1.[F:16][C:17]([F:38])([F:37])[C:18]1[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[CH:29][C:19]=1[CH2:20][N:21]1[CH2:26][CH2:25][CH:24]([CH:27]=O)[CH2:23][CH2:22]1.C([O-])(=O)C.[NH2+]1CCCCC1>CC(O)C>[F:38][C:17]([F:16])([F:37])[C:18]1[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[CH:29][C:19]=1[CH2:20][N:21]1[CH2:26][CH2:25][CH:24](/[CH:27]=[C:4]2/[C:5]([NH:7][CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[N:6][C:2](=[O:1])[S:3]/2)[CH2:23][CH2:22]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of tert-butyl N-(2-oxo-2,5-dihydro-1,3-thiazol-4-yl)glycinate (4.41 g) and 1-[2,4-bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde (5.00 g) in 2-propanol (50 mL) was added piperidinium acetate (2.14 g). The reaction mixture was stirred at 70° C. for 3 hr 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 (5.25 g).

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-0f630f07531f46c898fa20a0433f1ad0
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772277B2

Reaction notes

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