Methylamine → 4-(methylaminomethyl)benzonitrile

HRID 2184756Notes

Reaction equation

HRID 2184756 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[N:10])=[CH:5][CH:4]=1.[CH3:11][NH2:12]>C(#N)C>[CH3:11][NH:12][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[N:10])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 869964-(Bromomethyl)benzonitrile

Product 1

HCID 106068834-(methylaminomethyl)benzonitrileYield 38.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of α-bromo-p-tolunitrile (4.90 g, 25 mmol) in acetonitrile (50 mL) was added dropwise to a stirring solution of 40% aqueous methylamine (21.5 mL, 250 mmol) in acetonitrile (50 mL) at 0° C. The reaction mixture was stirred 0.5 h, then concentrated in vacuo. Water was added to the residue and extracted 2× with dichloromethane. The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to give 1.41 g of 4-(methylaminomethyl)benzonitrile as a yellow oil containing ˜30% of N,N-bis(4-benzonitrile)methyl-amine. The, aqueous was adjusted to pH>8 and extracted 2× with 9:1 dichloromethane:methanol. The combined extracts were dried over sodium sulfate, filtered, and concentrated in vacuo to give 1.13 g of pure 4-(methylamino)benzonitrile as a colorless oil.

Workup

  1. concentrationconcentrated in vacuo
  2. additionWater was added to the residue
  3. extractionextracted 2× with dichloromethane
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e447beb1e0584c5db7adf14b9415e490
Source dataset
uspto-grants-2002_06
Patent number
US06399604B1

Reaction notes

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