Reaktion #700955

Reaktionsgleichung

phenol

1-(2-chloroethyl) piperidine

potassium carbonate

→

title compound

Ausbeute 49.9%

Phenyl 2-Piperidinoethyl Ether Hydrochloride

Ausbeute 49.9%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated to reflux
2. 2
   TemperaturAfter refluxing for two hours
3. 3
   FiltrationThis mixture was filtered
4. 4
   Waschenthe solids washed with dimethylformamide (100 mL)
5. 5
   EinengenThe combined filtrates was concentrated in vacuo to a brown oil
6. 6
   workup.DISSOLUTIONThis oil was dissolved with ethyl acetate (400 mL)
7. 7
   Waschenthe resulting solution was washed with water (2×200 mL) and saturated brine (2×200 mL)
8. 8
   TrocknenThe ethyl acetate solution was dried over magnesium sulfate
9. 9
   Filtrationfiltered
10. 10
    Einengenconcentrated in vacuc to a brown oil
11. 11
    workup.DISSOLUTIONThis oil was dissolved in methanol (100 mL)
12. 12
    SonstigeThe resulting solution was evaporated to dryness in vacuo
13. 13
    SonstigeThe residue (74 g) was crystallized from 1-propanol (800 mL) and ethyl acetate (500 mL)

Vorschrift

A mixture of phenol (46.5 g), 1-(2-chloroethyl) piperidine (103.5 g), and potassium carbonate (207 g) in dimethylformamide (900 mL) was heated to reflux. After refluxing for two hours, the reaction mixture was allowed to cool to room temperature. This mixture was filtered, and the solids washed with dimethylformamide (100 mL). The combined filtrates was concentrated in vacuo to a brown oil. This oil was dissolved with ethyl acetate (400 mL), and the resulting solution was washed with water (2×200 mL) and saturated brine (2×200 mL). The ethyl acetate solution was dried over magnesium sulfate, filtered, and concentrated in vacuc to a brown oil. This oil was dissolved in methanol (100 mL), and the resulting solution acidified with 3% methanolic hydrochloric acid (prepared from acetyl chloride and methanol, 500 mL). The resulting solution was evaporated to dryness in vacuo. The residue (74 g) was crystallized from 1-propanol (800 mL) and ethyl acetate (500 mL) to give 59.6 g of the title compound as an off-white crystalline solid. Melting point 179-180° C.

Quelle