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Piperidinium acetate → HCID 178518154, compound

HRID 1620791
Notes
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Reaction equation

HRID 1620791 reaction equation
[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][NH:7][C:8]1[CH2:12][S:11][C:10](=[O:13])[N:9]=1.[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.C(OCC)(=O)C.CCCCCCC>[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][O:4][CH2:3][CH2:2][OH:1])=[N:9][C:10](=[O:13])[S:11]/2)[CH2:21][CH2:20]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 3014295Piperidinium acetateHCID 866786631-[2,4-Bis(trifluoromethyl)benzyl]piperidine-4-carbaldehydeHCID 178518155HCID 178518155, compound

Product 1

HCID 178518154HCID 178518154, compoundYield 62.2%

Reagents, catalysts & solvents 3

HCID 3776IsopropanolSolvent
HCID 8857
Ethyl Acetate
Solvent
HCID 8900HeptaneSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 4-{[2-(2-hydroxyethoxy)ethyl]amino}-1,3-thiazol-2(5H)-one (1.58 g) and 1-[2,4-bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde (2.89 g) in 2-propanol (30 mL) was added piperidinium acetate (1.12 g). The reaction mixture was stirred at 80° C. for 8 hr and concentrated. Water and ethyl acetate were 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) to give an oil. The oil was diluted with ethyl acetate (9 mL) and heptane (45 mL). The mixture was gradually cooled from 50° C. to 0° C., and the mixture was stirred for 6 hr. The precipitate was collected by filtration, and the obtained solid was washed with a mixed solution of ethyl acetate and heptane to give a white solid. The obtained white solid was recrystallized from ethyl acetate/heptane to give the title compound (2.53 g).

Workup

  1. concentrationconcentrated
  2. additionWater and ethyl acetate were 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. customto give an oil
  9. temperatureThe mixture was gradually cooled from 50° C. to 0° C.
  10. stirringthe mixture was stirred for 6 hr
  11. filtrationThe precipitate was collected by filtration
  12. washthe obtained solid was washed with a mixed solution of ethyl acetate and heptane
  13. customto give a white solid
  14. customThe obtained white solid was recrystallized from ethyl acetate/heptane

Sources & evidence

ORD record
ord-39ac21dbe4dd4b349b221c51f13c1542
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