Reaktion #1869224

Reaktionsgleichung

Water

Triethylamine

1-benzyl-4-(2-hydroxymethyl-phenyl)-piperidin-4-ol

methanesulfonyl chloride

→

oil

Ausbeute 94.7%

1′-Benzyl-3H-spiro[2-benzofuran-1,4′-piperidine]

Ausbeute 94.7%

Lösungsmittel

AcOEt

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was then refluxed for 4 h
2. 2
   SonstigeThe organic phase was separated
3. 3
   Sonstigedried
4. 4
   Sonstigeevaporated

Vorschrift

Crude 1-benzyl-4-(2-hydroxymethyl-phenyl)-piperidin-4-ol (180 g, 0.605 mol) was dissolved in THF (1000 mL). Triethylamine (176.18 mL, 1.27 mol) was added. A solution of methanesulfonyl chloride (33.03 mL, 0.424 mol) in THF (100 mL) was added slowly which caused an increase of the temperature from ambient to 53° C. The reaction was then refluxed for 4 h. Water (500 mL) and AcOEt (500 mL) were added to the reaction mixture. The organic phase was separated, dried and evaporated to give a brown oil (160 g).The crude product was purified by chromatography on silica gel with heptane/AcOEt 100:0 to 60:40 to give a light yellow solid (120 g, 71%). MS: m/z=280 [M+H]+.

Quelle