Sodium Cyanide → 4-Amino-1-t-butyl4-cyano-piperidine

HRID 353946Notes

Reaction equation

HRID 353946 reaction equation
[C:1]([N:5]1[CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[C-:12]#[N:13].[Na+].[NH4+:15].[Cl-]>N.CO>[NH2:15][C:8]1([C:12]#[N:13])[CH2:9][CH2:10][N:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:6][CH2:7]1

Participants

6

Reactant 3

HCID 8929Sodium CyanideHCID 25517Ammonium ChlorideHCID 738401-tert-Butyl-4-piperidone

Product 1

HCID 220632024-Amino-1-t-butyl4-cyano-piperidine

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolvent2×HCID 887MethanolSolvent2×

Procedure

1-t-Butyl-4-piperidone (1.3 g, 8.4 mmol, 1.0 equiv), NaCN (0.61 g, 12.6 mmol, 1.5 equiv), and NH4Cl (0.67 g, 12.6 mmol, 1.5 equiv) were combined in 34 mL of 2 M NH3 in MeOH. The mixture was refluxed for 2 h at which time an additional 34 mL of 2 M NH3 in MeOH was added followed by another 2 h at reflux. The mixture was cooled and filtered. The filtrate was concentrated in vacuo and the residue was triturated with CH2Cl2 and filtered again. The solution was concentrated to a thick red oil which was used without further purification; MS, m/z 182=M+1.

Workup

  1. additionwas added
  2. temperatureat reflux
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was triturated with CH2Cl2
  7. filtrationfiltered again
  8. concentrationThe solution was concentrated to a thick red oil which
  9. customwas used without further purification

Sources & evidence

ORD record
ord-e8a982318b2d414d96b2e2258c322c35
Source dataset
uspto-grants-2004_06
Patent number
US06756372B2

Reaction notes

Loading…