تفاعل #2122495

معادلة التفاعل

potassium cyanide

sodium bisulfite

1-ethoxy-piperidin-4-one

→

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

المذيبات

water

water

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر