Sodium Cyanide → 4-Amino-4-cyano-1,2-dimethyl-piperidine

HRID 915225Notes

Reaction equation

HRID 915225 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=O)[CH2:4][CH:3]1[CH3:9].[C-:10]#[N:11].[Na+].[NH4+:13].[Cl-]>N.CO>[NH2:13][C:5]1([C:10]#[N:11])[CH2:6][CH2:7][N:2]([CH3:1])[CH:3]([CH3:9])[CH2:4]1

Participants

6

Reactant 3

HCID 8929Sodium CyanideHCID 25517Ammonium ChlorideHCID 124240391,2-Dimethylpiperidin-4-one

Product 1

HCID 220631094-Amino-4-cyano-1,2-dimethyl-piperidine

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolvent2×HCID 887MethanolSolvent2×

Procedure

1,2-Dimethyl-4-piperidone (1.23 g, 9.67 mmol, 1.0 equiv) was dissolved in 39 mL of 2 M NH3 in MeOH (8 equiv NH3). To this solution was added NaCN (0.52 g, 10.6 mmol, 1.1 equiv) and NH4Cl (0.57 g, 10.6 mmol, 1.1 equiv). The resulting mixture was refluxed for 2 h at which time an additional 39 mL of 2 M NH3 in MeOH was added followed by an additional 2 h of reflux. The reaction was cooled and filtered. The filtrate was concentrated and taken up in 100 mL of CH2Cl2 giving more salt precipitate which was removed by a second filtration. The filtrate was then concentrated to thick orange oil (1.32 g, 89%). 1H NMR showed a 3 to 1 mixture of diastereomers of unknown configuration. The crude product was used without further purification; MS, m/z 154=M+1.

Workup

  1. additionwas added
  2. temperatureof reflux
  3. temperatureThe reaction was cooled
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customwas removed by a second filtration
  7. concentrationThe filtrate was then concentrated to thick orange oil (1.32 g, 89%)
  8. additionto 1 mixture of diastereomers of unknown configuration
  9. customThe crude product was used without further purification

Sources & evidence

ORD record
ord-c3988c24dfba4cb5a138e73c01c33e9e
Source dataset
uspto-grants-2007_09
Patent number
US07265132B2

Reaction notes

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