Ammonia → 4-Amino-1-(1-phenyl-ethyl)-piperidine-4-carbonitrile

HRID 2281656Notes

Reaction equation

HRID 2281656 reaction equation
[C:1]1([CH:7]([N:9]2[CH2:14][CH2:13][C:12](=O)[CH2:11][CH2:10]2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[NH4+:17].[NH3:18].[C-:19]#N.[Na+]>O>[NH2:17][C:12]1([C:19]#[N:18])[CH2:13][CH2:14][N:9]([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH3:8])[CH2:10][CH2:11]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8929Sodium CyanideHCID 25517Ammonium ChlorideHCID 119596271-(1-Phenylethyl)piperidin-4-one

Product 1

HCID 671207084-Amino-1-(1-phenyl-ethyl)-piperidine-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a mixture of 1-(1-phenyl-ethyl)-piperidin-4-one (10.9 g, 53.6 mmol), ammonium chloride (4.3 g, 80.4 mmol) and 30% aqueous ammonia solution (30 ml) in water (30 ml) at room temperature is added sodium cyanide (4.0 g, 81.6 mmol) portion wise. The reaction mixture is stirred at room temperature for 18 hours, then diluted with water and extracted with DCM. The organic phase is washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to obtain 4-Amino-1-(1-phenyl-ethyl)-piperidine-4-carbonitrile as a brown oil; [M+H]+ 230.

Workup

  1. extractionextracted with DCM
  2. washThe organic phase is washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-262da8a1ee6744db97d59a75e16a8e6b
Source dataset
uspto-grants-2015_09
Patent number
US09139586B2

Reaction notes

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