Acetyl chloride → 1-(4-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazin-1-yl)ethan-1-one

HRID 57565Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 57565
Cl.[CH3:2][C:3]1([CH3:22])[C:7]([CH3:9])([CH3:8])[O:6][B:5]([C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[CH:12][CH:11]=2)[O:4]1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:29](Cl)(=[O:31])[CH3:30]>C1COCC1>[CH3:9][C:7]1([CH3:8])[C:3]([CH3:22])([CH3:2])[O:4][B:5]([C:10]2[CH:11]=[CH:12][C:13]([N:16]3[CH2:17][CH2:18][N:19]([C:29](=[O:31])[CH3:30])[CH2:20][CH2:21]3)=[CH:14][CH:15]=2)[O:6]1

Komponenten

5

Edukt 3

HCID 6367Acetyl chlorideHCID 10796Cesium carbonateHCID 710936951-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazine hydrochloride

Produkt 1

HCID 532171411-(4-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazin-1-yl)ethan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl) piperazine hydrochloride (419 mg, 1.29 mmol) and cesiumcarbonate (1.27 g, 3.9 mmol) in THF (30 mL) was added acetyl chloride (0.5 mL, 6.5 mmol). Then the mixture was stirred at room temperature overnight, extracted with EA, washed with NaHCO3 solution and brine. The organic solution was concentrated and purified by flash column chromatography, eluting with PE/EA, to give product as a white solid. MS (m/z): 331 (M+H)+.

Aufarbeitung

  1. extractionextracted with EA
  2. washwashed with NaHCO3 solution and brine
  3. concentrationThe organic solution was concentrated
  4. custompurified by flash column chromatography
  5. washeluting with PE/EA
  6. customto give product as a white solid

Quellen und Nachweise

ORD-Eintrag
ord-f7f3a78685bb4c21806c8f77659c5485
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434726B2

Notizen zur Reaktion

Wird geladen…