Potassium Cyanide → HCID 86707843, compound

HRID 1844666Notes

Reaction equation

HRID 1844666 reaction equation
[CH3:1][O:2][N:3]1[CH2:8][CH2:7][CH:6]([CH2:9][CH:10]=[O:11])[CH2:5][CH2:4]1.OS([O-])=O.[Na+].[C-:17]#[N:18].[K+]>O>[OH:11][CH:10]([CH2:9][CH:6]1[CH2:7][CH2:8][N:3]([O:2][CH3:1])[CH2:4][CH2:5]1)[C:17]#[N:18]

Participants

5

Reactant 3

HCID 9032Potassium CyanideHCID 23665763Sodium BisulfiteHCID 86707842HCID 86707842, compound

Product 1

HCID 86707843HCID 86707843, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of (1-methoxy-piperidin-4-yl)-acetaldehyde (10 g, 63 mmol) and NaHSO3 (8.6 g, 83 mmol) in 210 ml of water was stirred at room temperature for 30 min. Then, a solution of KCN (6.2 g, 95 mmol) in 50 ml of water was added to the mixture. After the addition, the mixture was stirred at room temperature for another 10 h. The resulting mixture was extracted with CH2Cl2 five times. The combined organic layers were dried over sodium sulfate, filtered and concentrated under vacuum. The residue was purified by flash chromatography on silica gel. Yield: 2.1 g of 2-hydroxy-3-(1-methoxy-piperidin-4-yl)-propionitrile as a solid.

Workup

  1. additionAfter the addition
  2. stirringthe mixture was stirred at room temperature for another 10 h
  3. extractionThe resulting mixture was extracted with CH2Cl2 five times
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-0c94e59043d04684b9a6d25eaa546abf
Source dataset
uspto-grants-2015_02
Patent number
US08946453B2

Reaction notes

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