Reaktionsgleichung
O.[CH3:2][N:3]([CH3:23])[C@H:4]1[CH2:9][CH2:8][CH2:7][N:6]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:11]=2[N+:20]([O-])=O)[CH2:5]1>CO.[Pd]>[NH2:20][C:11]1[CH:12]=[C:13]([C:16]([F:17])([F:18])[F:19])[CH:14]=[CH:15][C:10]=1[N:6]1[CH2:7][CH2:8][CH2:9][C@H:4]([N:3]([CH3:23])[CH3:2])[CH2:5]1Komponenten
Versuchsvorschrift
A 500 mL parr pressure bottle was charged with palladium, 10 wt. % on activated carbon, 50% water wet (9.1 g, 8.6 mmol) under nitrogen. (S)—N,N-dimethyl-1-(2-nitro-4-(trifluoromethyl)phenyl)piperidin-3-amine (13.6 g, 43 mmol) was added as a solution in methanol via syringe, rinsing in with multiple methanol washes until the final volume was approximately 100 mL. The vessel was placed in a parr shaker, and treated with 2 atm H2 and shaken overnight. The reaction was flushed with nitrogen, and filtered through a pad of celite rinsing with 1.3 L of methanol and concentrated in vacuo. The oil was taken up in CH2Cl2, dried over Na2SO4, filtered, and concentrated in vacuo to give (S)-1-(2-amino-4-(trifluoromethyl)phenyl)-N,N-dimethylpiperidin-3-amine as a red oil. MS m/z=288 [M+H]+. Calc'd for C14H20F3N3: 287.
Aufarbeitung
- washrinsing in with multiple methanol washes until the final volume
- additiontreated with 2 atm H2
- customThe reaction was flushed with nitrogen
- filtrationfiltered through a pad of celite
- washrinsing with 1.3 L of methanol
- concentrationconcentrated in vacuo
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-e9c6783e1b4b438bb19eb1d78f5a9d29
- Quelldatensatz
- uspto-grants-2013_10
- Patentnummer
- US08557996B2
Verknüpfte Notizen
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