Sodium Cyanide → 4-Amino-4-cyano-1-phenyl-piperidine

HRID 1179166Notes

Reaction equation

HRID 1179166 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][C:10](=O)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C-:14]#[N:15].[Na+].[NH4+:17].[Cl-].N.CO>N.CO>[NH2:17][C:10]1([C:14]#[N:15])[CH2:11][CH2:12][N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][CH2:9]1

Participants

7

Reactant 4

HCID 8929Sodium CyanideHCID 25517Ammonium ChlorideHCID 4130091-Phenyl-4-piperidinoneHCID 21705897Ammonia methanol

Product 1

HCID 220633514-Amino-4-cyano-1-phenyl-piperidineYield 73.4%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

N-Phenyl-4-piperidone (2.3 g, 13 mmol, 1.0 equiv) was dissolved in 26 mL of 2 M NH3 in MeOH and NaCN (0.76 g, 15 mmol, 1.2 equiv) and NH4Cl (0.80 g, 15 mmol, 1.2 equiv) were added and the mixture was refluxed for 2 h at which time an additional 26 mL of 2 M NH3/MeOH was added followed by another 2 h of reflux. The reaction mixture was cooled and filtered. The filtrate was concentrated. The crude product was purified by flash chromatography on SiO2 eluting with 100% CH2Cl2 and 2% MeOH in CH2Cl2 to give the pure product (1.92 g) as a thick yellow oil which solidified on standing; MS, m/z 202=M+1.

Workup

  1. additionwas added
  2. temperatureof reflux
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customThe crude product was purified by flash chromatography on SiO2 eluting with 100% CH2Cl2 and 2% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-0e70be3f30804b529664417dd0858d6e
Source dataset
uspto-grants-2007_10
Patent number
US07279472B2

Reaction notes

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