1-Phenyl-1-propanone → 2-Amino-2-phenylbutanenitrile

HRID 2227451Notes

Reaction equation

HRID 2227451 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=O)[CH2:2][CH3:3].[C-:11]#[N:12].[K+].[NH4+:14].[Cl-]>[NH4+].[OH-].CCO>[NH2:14][C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)([CH2:2][CH3:3])[C:11]#[N:12]

Participants

6

Reactant 3

HCID 71481-Phenyl-1-propanoneHCID 9032Potassium CyanideHCID 25517Ammonium Chloride

Product 1

HCID 167944572-Amino-2-phenylbutanenitrileYield 81%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14923Ammonium HydroxideSolvent

Procedure

A mixture of propiophenone (30 g), KCN (34.5 g) and NH4Cl (30 g) in 180 mL of conc. NH4OH and 120 mL of EtOH is stirred at ambient temperature for 4 days. The reaction mixture is concentrated under vacuum and ether was added to the solid residue. The ether suspension is filtered and solid is washed with ether. Excess 1M of HCl in ether is added to the filtrate to precipitate HCl salt. The white solid is collected by filtration, washed with hexane and ether, and dried to give 29 g of the title compound as HCl salts. The white solid is basified with excess aqueous NaHCO3 and extracted with CH2Cl2. The extract is washed with brine, dried and concentrated to give 19 g of the titled compound as clear oil.

Workup

  1. concentrationThe reaction mixture is concentrated under vacuum and ether
  2. additionwas added to the solid residue
  3. filtrationThe ether suspension is filtered
  4. washsolid is washed with ether
  5. additionExcess 1M of HCl in ether is added to the filtrate
  6. customto precipitate HCl salt
  7. filtrationThe white solid is collected by filtration
  8. washwashed with hexane and ether
  9. customdried

Sources & evidence

ORD record
ord-dd4c8eef2dfc45b0af29199d8030147c
Source dataset
uspto-grants-2002_07
Patent number
US06413982B1

Reaction notes

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