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

HRID 974598

Reaction equation

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

Participants

Conditions

Temperature: -70 °C

Procedure

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.

Workup

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.

Sources & evidence

ORD record: ord-96d193196a4a4ba0bd61ef493f5e5a65
Source dataset: uspto-grants-1991_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05068231

Linked notes

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