Benzylamine → 4-(Benzylamino)benzonitrile

HRID 365715Notes

Reaction equation

HRID 365715 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[CH2:10]([NH2:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(#N)C>[CH2:6]([NH:7][C:14]1[CH:15]=[CH:16][C:11]([C:10]#[N:17])=[CH:12][CH:13]=1)[C:5]1[CH:8]=[CH:9][CH:2]=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 7504Benzylamine2×HCID 145174-Fluorobenzonitrile

Product 1

HCID 99425094-(Benzylamino)benzonitrileYield 72%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

4-Fluorobenzonitrile (6.0 g, 49.5 mmol) was dissolved in acetonitrile (60 ml), and benzylamine (10.6 g, 98.9 mmol) was added thereto, followed by stirring at 100° C. for 3 days. To complete the reaction, benzylamine (21.2 g, 198 mmol) was further added thereto, followed by stirring at 100° C. for 1 day. The solvent was removed under reduced pressure, water was added to the resulting residue, and the mixture was extracted with chloroform. After the organic layer was dried (over anhydrous magnesium sulfate), the drying agent was filtered off, and the filtrate was concentrated under reduced pressure. The resulting oily substances were purified by silica gel column chromatography (the substances were eluted with an increasing concentration of chloroform from chloroform/hexane=1/2 to chloroform/hexane=1/1) to give the title compound (7.42 g, 72%) as oily substances.

Workup

  1. additionwas further added
  2. stirringby stirring at 100° C. for 1 day
  3. customThe solvent was removed under reduced pressure, water
  4. additionwas added to the resulting residue
  5. extractionthe mixture was extracted with chloroform
  6. dry with materialAfter the organic layer was dried (over anhydrous magnesium sulfate)
  7. filtrationthe drying agent was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe resulting oily substances were purified by silica gel column chromatography (the substances
  10. washwere eluted with an increasing concentration of chloroform from chloroform/hexane=1/2 to chloroform/hexane=1/1)

Sources & evidence

ORD record
ord-c62496db747b455c93fae36e6f33e695
Source dataset
uspto-grants-2000_10
Patent number
US06127541

Reaction notes

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