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Piperidinium acetate → HCID 178518154, Verbindung

HRID 1620791
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1620791
[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
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

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

Produkt 1

HCID 178518154HCID 178518154, VerbindungAusbeute 62,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3776IsopropanolLösungsmittel
HCID 8857
Ethyl Acetate
Lösungsmittel
HCID 8900HeptaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-39ac21dbe4dd4b349b221c51f13c1542
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08772277B2

Notizen zur Reaktion

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