Piperidine → 1-[3-[3-(Trifluoromethyl)phenoxy]-1-azetidinylcarbonyl]piperidine

HRID 974597

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[CH2:30][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]1

Participants

Conditions

Temperature: -70 °C

Procedure

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, 6.0 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.

Workup

stirringstirred for 2 hr
customThe tetrahydrofuran was decanted
concentrationthen concentrated on a rotary evaporator
customto yield an amber oil, 6.0 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.

Sources & evidence

ORD record: ord-7b1896573f7d4ba6a0a5bb624f7954e5
Source dataset: uspto-grants-1991_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05068231

Linked notes

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