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

HRID 1022369Notes

Reaction equation

HRID 1022369 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 962WaterSolvent2×HCID 14923Ammonium HydroxideSolvent

Conditions

Temperature
25 °C

Procedure

To 10 g of N-methoxy-4-piperidone (J. Org. Chem. 1961, 26, 1867-74) in 240 ml ammoniumhydroxide 25% in water there are added 6.2 g of ammoniumchloride and 4.6 g of sodium cyanide. After stirring for 18 h at 25° C. the reaction mixture is diluted with 200 ml water and extracted with ethyl acetate. The organic phase is separated, dried over sodium sulphate, filtered and evaporated. 8.25 g of 4-amino-1-methoxy-piperidine-4-carbonitrile is obtained as light brow oil, which is used without further purification in the next step.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic phase is separated
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-f4e338df5ee04a02bd6e4dab3868329c
Source dataset
uspto-grants-2014_05
Patent number
US08722578B2

Reaction notes

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