Triethylamine → 4-Nitrophenyl 3-[(phenylcarbonyl)amino]-5-[4-(trifluoromethyl)phenyl]piperidine-1-carboxylate

HRID 876248

Reaktionsgleichung

[F:1][C:2]([F:25])([F:24])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][NH:13][CH2:12][CH:11]([NH:15][C:16](=[O:23])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:10]2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:33](Cl)(=[O:44])[O:34][C:35]1[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][CH:36]=1.C(=O)(O)[O-].[Na+]>ClCCl.O>[C:17]1([C:16]([NH:15][CH:11]2[CH2:10][CH:9]([C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:24])([F:1])[F:25])=[CH:8][CH:7]=3)[CH2:14][N:13]([C:33]([O:34][C:35]3[CH:36]=[CH:37][C:38]([N+:41]([O-:43])=[O:42])=[CH:39][CH:40]=3)=[O:44])[CH2:12]2)=[O:23])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

At 0° C., 1.5 g (4.3 mmol) of N-{5-[4-(trifluoromethyl)phenyl]piperidin-3-yl}benzamide and 1.2 ml (1.1 mmol) of triethylamine were initially charged in 131 ml of dichloromethane, and 868 mg (4.3 mmol) of 4-nitrophenyl chlorocarbonate were added slowly. The mixture was stirred at 0° C. for 2 h and then warmed to RT. Water and saturated aqueous sodium bicarbonate solution were added, and the reaction mixture was extracted. The organic phase was concentrated under reduced pressure and purified by column chromatography (cyclohexane/ethyl acetate 1:2). Yield: 1.95 g (88% of theory)

Aufarbeitung

temperaturewarmed to RT
extractionthe reaction mixture was extracted
concentrationThe organic phase was concentrated under reduced pressure
custompurified by column chromatography (cyclohexane/ethyl acetate 1:2)

Quellen und Nachweise

ORD-Eintrag: ord-5ad197d86fac4986b747e1ecf455f861
Quelldatensatz: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08987248B2

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