Hydrochloric Acid → 4-[(Benzylamino)methyl]benzonitrile

HRID 1941099Notes

Reaction equation

HRID 1941099 reaction equation
C([C:8](=[N:17]O)[C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=1)C1C=CC=CC=1.Cl>C(O)C>[CH2:8]([NH:17][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]#[N:14])=[CH:15][CH:16]=1)[C:9]1[CH:16]=[CH:15][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86751769HCID 86751769, compound

Product 1

HCID 123291374-[(Benzylamino)methyl]benzonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.44 g (15 mmol) of 4-(benzyloximinomethyl)benzonitrile in 120 ml of ethanol are cooled to -15° C. 4.46 g (48 mmol, 4.85 ml) of borane-pyridine complex are then added dropwise in the course of 10 minutes and then 26 ml of ethanolic HCl solution in the course of 20 minutes. After stirring at room temperature for 24 h, the resulting solid is filtered off, dissolved in dichloromethane and the solution is washed with water and sodium hydrogen carbonate solution. The organic phase is dried and concentrated in vacuo.

Workup

  1. addition4.46 g (48 mmol, 4.85 ml) of borane-pyridine complex are then added dropwise in the course of 10 minutes
  2. customin the course of 20 minutes
  3. filtrationthe resulting solid is filtered off
  4. dissolutiondissolved in dichloromethane
  5. washthe solution is washed with water and sodium hydrogen carbonate solution
  6. customThe organic phase is dried
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bb0550b839ee43c0a9551859d23e1f80
Source dataset
uspto-grants-1997_12
Patent number
US05703050

Reaction notes

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