Cesium carbonate → Tert-butyl 4-(6-cyanopyridin-3-yl)piperazine-1-carboxylate

HRID 2389272

Reaktionsgleichung

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-].[Cs+].[Cs+].CNC1CCCCC1NC>[Cu]I.CN1CCCC1=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

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

A mixture of the 5-bromopyridine-2-carbonitrile (0.957 g, 5.23 mmol), tert-butyl piperazine-1-carboxylate (1.36 g, 7.32 mmol), cesium carbonate (3.41 g, 10.5 mmol), racemic N,N′-dimethylcyclohexane-1,2-diamine (0.074 g, 0.52 mmol), and copper(I) iodide (0.010 mg, 0.052 mmol) was stirred with 13.1 mL of 1-methylpyrrolidin-2-one and purged with a stream of nitrogen. The reaction was heated to 120° C. for 8 hours. The mixture was diluted with dichloromethane (20 mL) and washed with water (3×20 mL). The organic layer was dried over sodium sulfate, filtered, concentrated, and subjected to purified by silica gel chromatography eluting with 0-50% EtOAc in hexanes. Collection of product containing fractions and removal of solvent yielded to yield tert-butyl 4-(6-cyanopyridin-3-yl)piperazine-1-carboxylate.

Aufarbeitung

custompurged with a stream of nitrogen
additionThe mixture was diluted with dichloromethane (20 mL)
washwashed with water (3×20 mL)
dry with materialThe organic layer was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customto purified by silica gel chromatography
washeluting with 0-50% EtOAc in hexanes
customCollection of product
additioncontaining
customfractions and removal of solvent
customyielded

Quellen und Nachweise

ORD-Eintrag: ord-c9d12e60c76c40658aeafca1f092aea5
Quelldatensatz: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08273737B2

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