Azetidine → 1-(1-Azetidinylcarbonyl)-3-[3-(trifluoromethyl)phenoxy]azetidine

HRID 1032127

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[CH2:28][CH2:27][CH2:26]1>O1CCCC1>[N:25]1([C:2]([N:4]2[CH2:7][CH:6]([O:8][C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=3)[CH2:5]2)=[O:3])[CH2:28][CH2:27][CH2:26]1

Komponenten

Reaktionsbedingungen

Temperatur: -70 °C

Versuchsvorschrift

A mixture of 5.6 g (0.02 mole) of 1-chlorocarbonyl-3-[3-(trifluoromethyl)phenoxy]azetidine and 3 g (0.027 mole) of potassium carbonate in 50 ml of tetrahydrofuran was treated with 1.26 g (0.022 mole) of azetidine added dropwise to the stirred mixture. After stirring for 15 min, the reaction was treated with 10 g of ice and stirred for an additional 72 hr. The tetrahydrofuran was decanted from the salt-paste and concentrated on a rotary evaporator to yield an oil, 6.3 g. This oil crystallized when cooled to -70° C. and was recrystallized from hexane yielding 5.1 g (85%) of fine white crystals, m.p. 65°-68° C.

Aufarbeitung

additionadded dropwise to the stirred mixture
stirringstirred for an additional 72 hr
customThe tetrahydrofuran was decanted from the salt-paste
concentrationconcentrated on a rotary evaporator
customto yield an oil, 6.3 g
customThis oil crystallized when
customwas recrystallized from hexane yielding 5.1 g (85%) of fine white crystals, m.p. 65°-68° C.

Quellen und Nachweise

ORD-Eintrag: ord-31d04e91b37144b987347977be261de1
Quelldatensatz: uspto-grants-1990_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04956359

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