Reaktion #85870

Reaktionsgleichung

1-(4-bromophenyl)piperidin-4-ol

sodium hydroxide

tert-butyl bromoacetate

→

material

Ausbeute 83.2%

tert-butyl 2-(1-(4-bromophenyl)piperidin-4-yloxy)acetate

Ausbeute 83.2%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto reach room temperature
2. 2
   SonstigeThe layers were separated
3. 3
   Waschenthe organic layer was washed twice with water (4 mL)
4. 4
   Trocknendried over sodium sulfate
5. 5
   Einengenconcentrated under vacuum and co-evaporated with petroleum ether
6. 6
   SonstigePurification of the crude material by flash column chromatography on silica gel (0-20% ethyl acetate in petroleum ether)

Vorschrift

Tetrabutylammonium bromide (1.06 g, 3.3 mmol) is added to a solution of 1-(4-bromophenyl)piperidin-4-ol (2.56 g, 10 mmol) in toluene (30 mL). The reaction mixture was cooled to 0° C. and aq. 35% sodium hydroxide (30 mL) was added followed by a drop-wise addition of tert-butyl bromoacetate (2.92 g, 15 mmol). The mixture was then allowed to reach room temperature and was stirred for 17 hours at this temperature. The layers were separated and the organic layer was washed twice with water (4 mL), dried over sodium sulfate, concentrated under vacuum and co-evaporated with petroleum ether. Purification of the crude material by flash column chromatography on silica gel (0-20% ethyl acetate in petroleum ether) yielded the desired pure material 3.08 g as pale yellow solid. MS (m/z): 372 (M+2)+

Quelle