Reaction #2122495

Reaction equation

potassium cyanide

sodium bisulfite

1-ethoxy-piperidin-4-one

→

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

Solvents

water

water

Conditions

Workup

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

Procedure

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.

Source