Reaktion #1697000

Reaktionsgleichung

methanol

3-[4-(imidazol-1-yl)phenoxy]piperidine

methanol

4-methoxy-1-naphthaldehyde

→

1-[(4-methoxynaphth-1-yl)methyl]piperidine

Ausbeute 16.8%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe methanol was evaporated
2. 2
   workup.ADDITIONthe residue diluted with ethyl acetate
3. 3
   Waschenwashed with water and brine
4. 4
   SonstigeEvaporation of the solvent in vacuo
5. 5
   Sonstigegave a crude product

Vorschrift

To a mixture of 3-[4-(imidazol-1-yl)phenoxy]piperidine (308 mg, 1.26 mmol), methanol (6.0 mL) was added 4-methoxy-1-naphthaldehyde (1.25 eq, 298 mg), followed by borane pyridine complex (0.196 mL, 1.25 eq.). The resulting mixture was stirred overnight. The methanol was evaporated, and the residue diluted with ethyl acetate, washed with water and brine. Evaporation of the solvent in vacuo gave a crude product. Flash column chromatography on silical gel with 1-2% methanol in methylene chloride afforded 3-[4-(imidazol-1-yl)phenoxy]-]-1-[(4-methoxynaphth-1-yl)methyl]piperidine (54 mg), 1H NMR(CDCl3) 8.30 (m, 2), 7.70 (s, 1), 7.50 (m, 2), 7.30 (s, 1), 7.20 (m, 4), 6.90 (m, 2), 6.70 (d, 2), 4.30 (m, 1), 4.00 (s, 3), 3.90 (AB q , 2), 3.10 (m, 1), 2.80 (m, 1), 2.10-2.30 (m, 3), 1.80 (m, 1), 1.40-1.70 (m, 2) ppm.

Quelle