1-Methylpiperazine → 4-Methyl-piperazine-1-carboxylic acid methyl-(4-nitro-3-piperidin-1-yl-phenyl)-amide
Reaktionsgleichung
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[CH3:13][NH:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[C:17]([N:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[CH:16]=1.CCN(C(C)C)C(C)C.[CH3:39][N:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1>C(Cl)Cl.C(Cl)(Cl)Cl>[CH3:13][N:14]([C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[C:17]([N:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[CH:16]=1)[C:5]([N:43]1[CH2:44][CH2:45][N:40]([CH3:39])[CH2:41][CH2:42]1)=[O:11]Komponenten
7
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
To a solution of triphosgene (40.6 mg, 0.13 mmol) in 2 mL of CH2Cl2 was added methyl-(4-nitro-3-piperidin-1-yl-phenyl)-amine (88 mg, 0.37 mmol) and DIEA (38 μL, 0.22 mmol) in 2 mL of CH2Cl2 over a 15 min. period. A solution of N-methylpiperazine (1.2 eq, 41 μL) and DIEA (38 μL, 0.22 mmol) in 1.5 mL of CH2Cl2 were then added via cannula and stirring was continued for 10 min. The reaction was diluted with CHCl3 (50 mL) and washed with satd aq NaHCO3 (50 mL). The organic layer was dried (Na2SO4) and concentrated in vacuo to give 115 mg (86%) of the title compound a yellow oil. Mass spectrum (ESI, m/z): Calcd. for C18H27N5O3, 362.2 (M+H), found 362.2.
Aufarbeitung
- washwashed with satd aq NaHCO3 (50 mL)
- dry with materialThe organic layer was dried (Na2SO4)
- concentrationconcentrated in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-be62f9a6e6b44a6cafaf1c26c25b354d
- Quelldatensatz
- uspto-grants-2010_04
- Patentnummer
- US07705042B2
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