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Piperidinium acetate → HCID 178456914, compound

HRID 1620735
Notes
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Reaction equation

HRID 1620735 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.[CH2:24]([NH:27][C:28]1[CH2:32][S:31][C:30](=[O:33])[N:29]=1)[C:25]#[CH:26].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:32]2/[C:28]([NH:27][CH2:24][C:25]#[CH:26])=[N:29][C:30](=[O:33])[S:31]/2)[CH2:8][CH2:7]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 3014295Piperidinium acetateHCID 866786631-[2,4-Bis(trifluoromethyl)benzyl]piperidine-4-carbaldehydeHCID 178456890HCID 178456890, compound

Product 1

HCID 178456914HCID 178456914, compoundYield 58.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 1-[2,4-bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde (35.0 g) and 4-(prop-2-yn-1-ylamino)-1,3-thiazol-2(5H)-one (23.9 g) in 2-propanol (400 mL) was added piperidinium acetate (15.0 g) at room temperature. The reaction mixture was stirred at 80° C. for 4 hr and concentrated under reduced pressure. Ethyl acetate was added to the residue, and the precipitate was removed by filtration. Water and ethyl acetate were 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 the obtained solid was washed with diisopropyl ether to give a solid. The obtained solid was recrystallized from ethyl acetate/heptane/diisopropyl ether to give the title compound (28.9 g).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionEthyl acetate was added to the residue
  3. customthe precipitate was removed by filtration
  4. additionWater and ethyl acetate were 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. washthe obtained solid was washed with diisopropyl ether
  11. customto give a solid
  12. customThe obtained solid was recrystallized from ethyl acetate/heptane/diisopropyl ether

Sources & evidence

ORD record
ord-1e2d47cd8ca749938a5601a6bf0468e5
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08772277B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes