Piperidine → 1-[3-[3-(Trifluoromethyl)phenoxy]-1-azetidinylcarbonyl]piperidine
Reaktionsgleichung
Cl[C:2]([N:4]1[CH2:7][CH:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[CH2:5]1)=[O:3].C(=O)([O-])[O-].[K+].[K+].[NH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>O1CCCC1.C1C=CC=CC=1>[F:16][C:15]([F:18])([F:17])[C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=1)[O:8][CH:6]1[CH2:7][N:4]([C:2]([N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[O:3])[CH2:5]1Komponenten
6
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- -70 °C
Versuchsvorschrift
A solution of 5.6 g (0.02 mole) of 1-chlorocarbonyl-3-[3-(trifluoromethyl)phenoxy]azetidine in 50 ml of tetrahydrofuran was treated with 3 g (0.022 mole) of potassium carbonate and while stirring, 1.9 g (0.022 mole) of piperidine was added dropwise. The mixture was then treated with 10 g of ice and stirred for 2 hr. The tetrahydrofuran was decanted then concentrated on a rotary evaporator to yield an amber oil, 6.9 g. The oil was dissolved in benzene, washed with dilute acid then water, dried over magnesium sulfate and concentrated in vacuo. This oil crystallized when cooled to -70° C. and was recrystallized from hexane with charcoal treatment at 0° C. yielding pale tan crystals, 4.5 g (68.5%), m.p. 50°-52° C.
Aufarbeitung
- stirringstirred for 2 hr
- customThe tetrahydrofuran was decanted
- concentrationthen concentrated on a rotary evaporator
- customto yield an amber oil, 6.9 g
- washwashed
- additionwith dilute acid
- dry with materialwater, dried over magnesium sulfate
- concentrationconcentrated in vacuo
- customThis oil crystallized when
- customwas recrystallized from hexane with charcoal treatment at 0° C.
- customyielding pale tan crystals, 4.5 g (68.5%), m.p. 50°-52° C.
Quellen und Nachweise
- ORD-Eintrag
- ord-56e478babd9d402aa2debdaede88074e
- Quelldatensatz
- uspto-grants-1993_02
- Patentnummer
- US05183902
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