反応 #2122495

反応方程式

potassium cyanide

sodium bisulfite

1-ethoxy-piperidin-4-one

→

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

溶媒

water

water

反応条件

後処理

1. 1
   workup.ADDITIONAfter the addition
2. 2
   workup.WAITleft
3. 3
   workup.STIRRINGstirring for 24 hours
4. 4
   抽出The mixture was thoroughly extracted with ethyl acetate (4×30 ml)
5. 5
   洗浄the combined organic layers were washed twice with brine (2×30 ml)
6. 6
   乾燥dried over sodium sulfate
7. 7
   ろ過After filtration and concentration under vacuum
8. 8
   その他the residue was purified by column chromatography on silica gel

実験手順

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.

出典