Reaktion #2007008

Reaktionsgleichung

4-hydroxy-N-methylpiperidine

potassium tert-butoxide

4-Fluoro-3-(trifluoromethyl)benzonitrile

→

pure product

Ausbeute 55.1%

4-[(1-Methylpiperidin-4-yl)oxy]-3-(trifluoromethyl)benzonitrile

Ausbeute 55.1%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction mixture was stirred at ambient temperature for 1 h
2. 2
   SonstigeThe solvent was removed in vacuo
3. 3
   Sonstigethe residue was partitioned between a 1 M NaOH solution and ethyl acetate
4. 4
   TrocknenThe organic layer was dried (Na2SO4)
5. 5
   Sonstigeevaporated
6. 6
   SonstigeThe residue was purified by column chromatography on silica gel (eluent: CHCl3/MeOH/conc. NH3, 95:5:0.5)

Vorschrift

A mixture of 4-hydroxy-N-methylpiperidine (133 mg, 1.15 mmol) and potassium tert-butoxide (150 mg, 1.27 mmol) in tetrahydrofuran (2.5 mL) was stirred under nitrogen for 10 min. 4-Fluoro-3-(trifluoromethyl)benzonitrile (218 mg, 1.15 mmol) was added, and the reaction mixture was stirred at ambient temperature for 1 h. The solvent was removed in vacuo, and the residue was partitioned between a 1 M NaOH solution and ethyl acetate. The organic layer was dried (Na2SO4) and evaporated. The residue was purified by column chromatography on silica gel (eluent: CHCl3/MeOH/conc. NH3, 95:5:0.5) affording 0.18 g (54% yield) of the pure product as a colourless solid. MS (APCI) m/z 285 [M+H]. 1H NMR (400 MHz, DMSO-D6) δ ppm 1.67-1.74 (m, 2 H), 1.89-1.95 (m, 2 H), 2.16 (s, 3 H), 2.26-2.31 (m, 2 H), 2.44-2.48 (m, 2 H), 4.78-4.82 (m, 1 H), 7.51 (d, J=8.8 Hz, 1 H), 8.08 (dd, J=8.8, 2.0 Hz, 1 H), 8.14 (d, J=2.0 Hz, 1 H).

Quelle