Reaktion #2122495

Reaktionsgleichung

potassium cyanide

sodium bisulfite

1-ethoxy-piperidin-4-one

→

1-Ethoxy-4-hydroxy-piperidine-4-carbonitrile

Lösungsmittel

water

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter the addition
2. 2
   workup.WAITleft
3. 3
   workup.STIRRINGstirring for 24 hours
4. 4
   ExtraktionThe mixture was thoroughly extracted with ethyl acetate (4×30 ml)
5. 5
   Waschenthe combined organic layers were washed twice with brine (2×30 ml)
6. 6
   Trocknendried over sodium sulfate
7. 7
   FiltrationAfter filtration and concentration under vacuum
8. 8
   Sonstigethe residue was purified by column chromatography on silica gel

Vorschrift

A solution of sodium bisulfite (10.7 g, 103 mmol) in 10 ml of water was cooled in an ice bath. Then, 1-ethoxy-piperidin-4-one (12.3 g, 86 mmol, prepared according to J. Org. Chem. 1961, 26, 1867-74) was added dropwise. After the addition, the mixture was stirred for another 30 min. A solution of potassium cyanide (8.4 g, 129 mmol) in 10 ml of water was added slowly, the reaction mixture was warmed up to room temperature and left stirring for 24 hours. The mixture was thoroughly extracted with ethyl acetate (4×30 ml) and the combined organic layers were washed twice with brine (2×30 ml) and dried over sodium sulfate. After filtration and concentration under vacuum, the residue was purified by column chromatography on silica gel. Yield: 13.2 g of 1-ethoxy-4-hydroxy-piperidine-4-carbonitrile (title compound P4.9) as a light yellow oil.

Quelle