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Piperidinium acetate → HCID 178484616, compound

HRID 1620640
Notes
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Reaction equation

HRID 1620640 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]([CH3:36])[C:26](=[O:35])[CH2:27][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][CH2:27][C:26]([N:25]([CH3:36])[CH3:24])=[O:35])=[N:30][C:31](=[O:34])[S:32]/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 178484615HCID 178484615, compound

Product 1

HCID 178484616HCID 178484616, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-[2,4-bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde (6.57 g) and N,N-dimethyl-N2-(2-oxo-2,5-dihydro-1,3-thiazol-4-yl)glycinamide (4.68 g) in 2-propanol (60 mL) was added piperidinium acetate (2.81 g). 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 (NH, ethyl acetate/hexane). The obtained solid was washed with diisopropyl ether and recrystallized from ethyl acetate/heptane to give the title compound (5.62 g).

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 (NH, ethyl acetate/hexane)
  8. washThe obtained solid was washed with diisopropyl ether
  9. customrecrystallized from ethyl acetate/heptane

Sources & evidence

ORD record
ord-fa0c19316a7941ffa277353e6a4e9081
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