Piperidinium acetate → HCID 178462001, compound

HRID 1620683Notes

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.[CH3:24][N:25]([CH3:37])[C:26](=[O:36])[C@H:27]([CH3:35])[NH:28][C:29]1[CH2:33][S:32][C:31](=[O:34])[N:30]=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:33]2/[C:29]([NH:28][C@H:27]([C:26]([N:25]([CH3:24])[CH3:37])=[O:36])[CH3:35])=[N:30][C:31](=[O:34])[S:32]/2)[CH2:8][CH2:7]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1-[2,4-bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde (305 mg) and N,N-dimethyl-N2-(2-oxo-2,5-dihydro-1,3-thiazol-4-yl)-L-alaninamide (213 mg) in 2-propanol (2 mL) was added piperidinium acetate (144 mg) at room temperature. The reaction mixture was stirred at 60° C. overnight. The solvent was evaporated, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (180 mg).

Workup

customThe solvent was evaporated
customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-c6f26991b2c34b268cf51258d121acb1
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772277B2

Reaction notes

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