Piperidinium acetate → HCID 178504889, compound

HRID 1620697Notes

Reaction equation

HRID 1620697 reaction equation
[CH3:1][S:2]([CH2:5][CH2:6][NH:7][C:8]1[CH2:12][S:11][C:10](=[O:13])[N:9]=1)(=[O:4])=[O:3].[F:14][C:15]([F:36])([F:35])[C:16]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][C:17]=1[CH2:18][N:19]1[CH2:24][CH2:23][CH:22]([CH:25]=O)[CH2:21][CH2:20]1.C([O-])(=O)C.[NH2+]1CCCCC1>CC(O)C>[F:36][C:15]([F:14])([F:35])[C:16]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][C:17]=1[CH2:18][N:19]1[CH2:24][CH2:23][CH:22](/[CH:25]=[C:12]2/[C:8]([NH:7][CH2:6][CH2:5][S:2]([CH3:1])(=[O:3])=[O:4])=[N:9][C:10](=[O:13])[S:11]/2)[CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 3014295Piperidinium acetateHCID 866786631-[2,4-Bis(trifluoromethyl)benzyl]piperidine-4-carbaldehydeHCID 178504888HCID 178504888, compound

Product 1

HCID 178504889HCID 178504889, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-{[2-(methylsulfonyl)ethyl]amino}-1,3-thiazol-2(5H)-one (1.39 g) and 1-[2,4-bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde (1.77 g) in 2-propanol (20 mL) was added piperidinium acetate (757 mg). The reaction mixture was stirred at 80° C. for 3 hr and concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with water and 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 recrystallized from ethyl acetate/heptane to give the title compound (1.6 g).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionWater was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water and 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/hexane)
  8. customthe obtained solid was recrystallized from ethyl acetate/heptane

Sources & evidence

ORD record
ord-4bdc68c02fa64a32a867e3e1ce04f947
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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