Potassium Carbonate → 4-Phenyl-1-[3-[3-(trifluoromethyl)phenoxy]-1-azetidinylcarbonyl]piperidine

HRID 2081475

Reaktionsgleichung

[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=1)[O:6][CH:7]1[CH2:10][N:9]([C:11](Cl)=[O:12])[CH2:8]1.C(=O)([O-])[O-].[K+].[K+].[C:25]1([CH:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O1CCCC1.O>[C:25]1([CH:31]2[CH2:32][CH2:33][N:34]([C:11]([N:9]3[CH2:10][CH:7]([O:6][C:5]4[CH:14]=[CH:15][CH:16]=[C:3]([C:2]([F:18])([F:17])[F:1])[CH:4]=4)[CH2:8]3)=[O:12])[CH2:35][CH2:36]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

A mixture of 2.8 g (0.01 mole) of 3-[3-(trifluoromethyl)phenoxy]-1-azetidinecarbonyl chloride and 1.4 g (0.01 mole) of potassium carbonate in 25 ml of tetrahydrofuran was stirred for 10 min then treated with 1.6 g (0.01 mole) of 4-phenylpiperidine. After stirring for 30 min, approximately 2 g of ice was added and stirring continued for 18 hr. The reaction mixture was diluted with 200 ml of water and the oil which separated was extracted into methylene chloride (2×50 ml). The extracts were combined, dried and concentrated in vacuo to yield 4.95 g of crude oil which solidified when cooled to -78° C. Recrystallization from isopropyl ether yielded 1.5 g (37%) of coarse white crystals, m.p. 72°-74° C.

Aufarbeitung

stirringAfter stirring for 30 min
stirringstirring
waitcontinued for 18 hr
customthe oil which separated
extractionwas extracted into methylene chloride (2×50 ml)
customdried
concentrationconcentrated in vacuo
customto yield 4.95 g of crude oil which
customRecrystallization from isopropyl ether

Quellen und Nachweise

ORD-Eintrag: ord-4ec25f5c1eee4268b74bdfe813a50e7e
Quelldatensatz: uspto-grants-1993_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05183902

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