Piperidinium acetate → HCID 178456922, compound

HRID 1620605Notes

Reaction equation

HRID 1620605 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([CH:12]=O)[CH2:8][C:7]1=[O:14].[CH2:25]([NH:28][C:29]1[CH2:33][S:32][C:31](=[O:34])[N:30]=1)[C:26]#[CH:27].C([O-])(=O)C.[NH2+]1CCCCC1>CC(O)C>[F:24][C:2]([F:1])([F:23])[C:3]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][CH:9](/[CH:12]=[C:33]2/[C:29]([NH:28][CH2:25][C:26]#[CH:27])=[N:30][C:31](=[O:34])[S:32]/2)[CH2:8][C:7]1=[O:14]

Participants

5

Reactant 3

HCID 3014295Piperidinium acetateHCID 866787751-[2,4-Bis(trifluoromethyl)benzyl]-2-oxopiperidine-4-carbaldehydeHCID 178456890HCID 178456890, compound

Product 1

HCID 178456922HCID 178456922, compoundYield 34.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-[2,4-bis(trifluoromethyl)benzyl]-2-oxopiperidine-4-carbaldehyde (1.00 g) and 4-(prop-2-yn-1-ylamino)-1,3-thiazol-2(5H)-one (0.66 g) in 2-propanol (10 mL) was added piperidinium acetate (0.41 g). The reaction mixture was stirred at 80° C. for 4 hr and concentrated. Ethyl acetate was added to the residue, and the precipitate was removed. Water was added to the filtrate, 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/hexane) and recrystallized from ethanol/heptane to give the title compound (0.48 g).

Workup

  1. concentrationconcentrated
  2. additionEthyl acetate was added to the residue
  3. customthe precipitate was removed
  4. additionWater was added to the filtrate
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
  10. customrecrystallized from ethanol/heptane

Sources & evidence

ORD record
ord-28694367f6554fbea65e944be6c54436
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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