Sodium Cyanide → 4-Amino-1-methoxy-piperidine-4-carbonitrile

HRID 1962357Notes

Reaction equation

HRID 1962357 reaction equation
[CH3:1][O:2][N:3]1[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1.[Cl-].[NH4+:11].[C-:12]#[N:13].[Na+]>[OH-].[NH4+].O>[NH2:11][C:6]1([C:12]#[N:13])[CH2:7][CH2:8][N:3]([O:2][CH3:1])[CH2:4][CH2:5]1

Participants

6

Reactant 3

HCID 8929Sodium CyanideHCID 25517Ammonium ChlorideHCID 199366531-Methoxypiperidin-4-one

Product 1

HCID 596145944-Amino-1-methoxy-piperidine-4-carbonitrileYield 68.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14923Ammonium HydroxideSolvent

Conditions

Temperature
25 °C

Procedure

To 10 g of N-methoxy-4-piperidone (Journal of Organic Chemistry (1961), 26, 1867-74) in 240 ml of ammonium hydroxide (25% in water) was added 6.2 g of ammonium chloride and 4.6 g of sodium cyanide. After stirring for 18 hours at 25° C. the reaction mixture was diluted with 200 ml of water and extracted with ethyl acetate. The organic phase was separated, dried over sodium sulfate and evaporated. 8.25 g of 4-amino-1-methoxy-piperidine-4-carbonitrile was obtained as a light brown oil, which was used without further purification in the next step.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic phase was separated
  3. dry with materialdried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-6f889f405fcb447ab51798719fd853e6
Source dataset
uspto-grants-2013_04
Patent number
US08415369B2

Reaction notes

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