Potassium Cyanide → 1-Ethoxy-4-hydroxy-piperidine-4-carbonitrile

HRID 2035313Notes

Reaction equation

HRID 2035313 reaction equation
S(=O)(O)[O-].[Na+].[CH2:6]([O:8][N:9]1[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]1)[CH3:7].[C-:16]#[N:17].[K+]>O>[CH2:6]([O:8][N:9]1[CH2:14][CH2:13][C:12]([OH:15])([C:16]#[N:17])[CH2:11][CH2:10]1)[CH3:7]

Participants

5

Reactant 3

HCID 9032Potassium CyanideHCID 23665763Sodium BisulfiteHCID 570965291-Ethoxypiperidin-4-one

Product 1

HCID 866633011-Ethoxy-4-hydroxy-piperidine-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

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.

Workup

  1. additionAfter the addition
  2. waitleft
  3. stirringstirring for 24 hours
  4. extractionThe mixture was thoroughly extracted with ethyl acetate (4×30 ml)
  5. washthe combined organic layers were washed twice with brine (2×30 ml)
  6. dry with materialdried over sodium sulfate
  7. filtrationAfter filtration and concentration under vacuum
  8. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-e052a243bc8b449595334c5c76e1f5de
Source dataset
uspto-grants-2013_11
Patent number
US08574607B2

Reaction notes

Loading…