Ethyl Acetate → Tert-butyl 4-(6-cyanopyridin-3-yl)piperazine-1-carboxylate

HRID 1465468

Reaktionsgleichung

Reaktionsgleichung von HRID 1465468
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[N:10]1([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O>[C:8]([C:5]1[N:6]=[CH:7][C:2]([N:13]2[CH2:12][CH2:11][N:10]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14]2)=[CH:3][CH:4]=1)#[N:9]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 8171545-Bromopyridine-2-carbonitrile

Produkt 1

HCID 67030211Tert-butyl 4-(6-cyanopyridin-3-yl)piperazine-1-carboxylateAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a solution of 5-bromopyridine-2-carbonitrile (551.3 mg, 3.012 mmol) in anhydrous dimethylformamide (6.0 ml) were added tert-butyl piperazine-1-carboxylate (670.6 mg, 3.601 mmol) and potassium carbonate (829.0 mg, 5.998 mmol). The mixture was stirred at 120° C. for 63 hrs and cooled to room temperature. Ethyl acetate (30 ml) was added, and the precipitate was collected by filtration. Water (30 ml) was added to the filtrate, and the precipitated solid was collected by filtration and dried under reduced pressure to give tert-butyl 4-(6-cyanopyridin-3-yl)piperazine-1-carboxylate (642.9 mg, yield 74.0%) as a slightly yellow solid.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. filtrationthe precipitate was collected by filtration
  3. additionWater (30 ml) was added to the filtrate
  4. filtrationthe precipitated solid was collected by filtration
  5. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a5d1d698b94045d8850b11c2a3c02f10
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US08999989B2

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