1-[(6-Chloropyridin-3-yl)methyl]-4-methylpiperazine → 5-((4-Methylpiperazin-1-yl)methyl)pyridin-2-amine

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Reaktionsgleichung

Cl[C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.C[Si]([N-:45][Si](C)(C)C)(C)C.[Li+]>C1COCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:15][N:12]1[CH2:13][CH2:14][N:9]([CH2:8][C:5]2[CH:4]=[CH:3][C:2]([NH2:45])=[N:7][CH:6]=2)[CH2:10][CH2:11]1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

To a sealed tube under nitrogen was added 1-((6-chloropyridin-3-ylmethyl)-4-methylpiperazine (13.5 g, 59.8 mmol, Eq: 1.00), 2-(dicyclohexylphosphino)biphenyl (4.19 g, 12.0 mmol, Eq: 0.20), tris(dibenzylideneacetone)-dipalladium (0) (5.48 g, 5.98 mmol, Eq: 0.10), and lithium bis(trimethylsilyl)amide, 150 ml of a 1.0M solution in THF. An additional 150 ml THF was added. The flask was degassed with argon. The flask was capped and the reaction heated at 100° C. overnight. 3M HCl was added along with DCM to the material and the layers were separated. The aqueous layer was bacidified with 3M NaOH. The aqueous layer was then extracted 3 times with DCM to provide 3.2 g (25.9%) of a yellow powder which was used without further purification.

Aufarbeitung

customThe flask was degassed with argon
customThe flask was capped
addition3M HCl was added along with DCM to the material
customthe layers were separated
extractionThe aqueous layer was then extracted 3 times with DCM

Quellen und Nachweise

ORD-Eintrag: ord-b807e7a5a7cd478ba2dc2ae8f72d07d6
Quelldatensatz: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08940741B2

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