Piperidinium acetate → HCID 178484552, compound

HRID 1620689Notes

Reaction equation

HRID 1620689 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])[CH2:27][CH2:28][NH:29][C:30]1[CH2:34][S:33][C:32](=[O:35])[N:31]=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:34]2/[C:30]([NH:29][CH2:28][CH2:27][C:26]([N:25]([CH3:24])[CH3:37])=[O:36])=[N:31][C:32](=[O:35])[S:33]/2)[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 3014295Piperidinium acetateHCID 866786631-[2,4-Bis(trifluoromethyl)benzyl]piperidine-4-carbaldehydeHCID 178484550HCID 178484550, compound

Product 1

HCID 178484552HCID 178484552, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-[2,4-bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde (520 mg) and N,N-dimethyl-N3-(2-oxo-2,5-dihydro-1,3-thiazol-4-yl)-β-alaninamide (330 mg) in 2-propanol (60 mL) was added piperidinium acetate (223 mg). The reaction mixture was stirred at 80° C. for 4 hr and concentrated. Water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/methanol). The obtained solid was recrystallized from ethyl acetate/heptane to give the title compound (356 mg).

Workup

  1. concentrationconcentrated
  2. additionWater was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/methanol)
  8. customThe obtained solid was recrystallized from ethyl acetate/heptane

Sources & evidence

ORD record
ord-f3d08d24b7d1481eb59bc07bdeae7e92
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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