Potassium Cyanide → HCID 86707846, compound

HRID 1844679Notes

Reaction equation

HRID 1844679 reaction equation
OS([O-])=O.[Na+].[CH3:6][O:7][N:8]1[CH2:13][CH2:12][CH:11]([CH:14]=[O:15])[CH2:10][CH2:9]1.[C-:16]#[N:17].[K+]>O>[OH:15][CH:14]([CH:11]1[CH2:12][CH2:13][N:8]([O:7][CH3:6])[CH2:9][CH2:10]1)[C:16]#[N:17]

Participants

5

Reactant 3

HCID 9032Potassium CyanideHCID 23665763Sodium BisulfiteHCID 86707845HCID 86707845, compound

Product 1

HCID 86707846HCID 86707846, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

NaHSO3 (11.4 g, 110 mmol) was added to a solution of 1-methoxy-piperidine-4-carbaldehyde (7.5 g, 52.4 mmol) in water (200 mL). After the mixture was stirred at room temperature for 3 h, a solution of KCN (7.2 g, 110 mmol) in water (100 mL) was added to the mixture. The reaction mixture was stirred for 2 h. Then the mixture was extracted with ethyl acetate three times. The combined organic layers were dried over sodium sulfate, concentrated under vacuum to dryness and the residue was purified by column chromatography on silica gel. Yield: 6.2 g of hydroxy-(1-methoxy-piperidin-4-yl)-acetonitrile as an oil.

Workup

  1. stirringThe reaction mixture was stirred for 2 h
  2. extractionThen the mixture was extracted with ethyl acetate three times
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated under vacuum to dryness
  5. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-1aab6cf6e07541ea922a5b021148b1e0
Source dataset
uspto-grants-2015_02
Patent number
US08946453B2

Reaction notes

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