Potassium Carbonate → HCID 86670955, Verbindung

HRID 515318Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 515318
[NH:1]1[CH2:6][CH2:5][CH:4]([S:7][C:8]2[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.Br[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([OH:32])([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[NH2:12][C:11]1[CH:13]=[CH:14][C:8]([S:7][CH:4]2[CH2:3][CH2:2][N:1]([CH2:16][C:17]3[CH:18]=[CH:19][C:20]([C:23]([OH:32])([C:24]([F:25])([F:26])[F:27])[C:28]([F:29])([F:30])[F:31])=[CH:21][CH:22]=3)[CH2:6][CH2:5]2)=[CH:9][CH:10]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 235273962-[4-(Bromomethyl)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-olHCID 61684683HCID 61684683, Verbindung

Produkt 1

HCID 86670955HCID 86670955, VerbindungAusbeute 62,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

4-(Piperidin-4-ylthio)aniline (6.69 mmol, 1.3946 g), 2-(4-(bromomethyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (6.69 mmol, 2.256 g), and potassium carbonate (13.39 mmol, 1.850 g) were combined in acetonitrile (20 mL) and the reaction mixture stirred at room temperature for 1 hour. The reaction mixture was concentrated under vacuum, and partitioned between dichloromethane and water. The organic layer was separated, dried, and concentrated under vacuum. The residue was purified by silica column chromatography (eluting with 2.5-5% methanol/dichloromethane gradient) to afford the title compound (1.93 g). MS m/z 465.0 [M+H]+

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. custompartitioned between dichloromethane and water
  3. customThe organic layer was separated
  4. customdried
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by silica column chromatography (eluting with 2.5-5% methanol/dichloromethane gradient)

Quellen und Nachweise

ORD-Eintrag
ord-ccf26deccabd462db773adad07d842ae
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108939B2

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