Reaktion #10272

Reaktionsgleichung

acetophenone oxime

water

4-(2-chloroethyl)morpholine hydrochloride

sodium hydroxide

water

→

acetophenone O-[2-((morpholin-4-yl))ethyl]oxime

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   workup.DISSOLUTIONto dissolve all the salts
3. 3
   Sonstigethe layers were separated
4. 4
   Extraktionthe aqueous layer was extracted with toluene
5. 5
   TrocknenThe organic layers were dried (MgSO4)
6. 6
   Einengenconcentrated in vacuo
7. 7
   SonstigeThe residue was purified by flash chromatography (SiO2, CH2Cl2/MeOH 95/5)

Vorschrift

To a solution of acetophenone oxime (20 g) in toluene (700 mL) was added subsequently tetrabutylammonium bromide (4.77 g), water (8 mL), 4-(2-chloroethyl)morpholine hydrochloride (30.31 g) and finally 50% sodium hydroxide (aq, 52 mL). The resulting mixture was heated at 75° C. overnight. After cooling to room temperature water was added, to dissolve all the salts, the layers were separated, and the aqueous layer was extracted with toluene. The organic layers were dried (MgSO4), and concentrated in vacuo. The residue was purified by flash chromatography (SiO2, CH2Cl2/MeOH 95/5) to afford acetophenone O-[2-((morpholin-4-yl))ethyl]oxime as an oil. The obtained oil was dissolved in 6M HCl (aq, 500 mL) and heated under reflux for 5 hours and subsequently stirred overnight at room temperature. The mixture was extracted with ether and concentrated in vacuo. The residue was crystallized from ethanol, to afford O-[2-((morpholin-4-yl))ethyl]hydroxylamine dihydrochloride. 24.8 g (77%)

Quelle