Methylamine → 4-(methylaminomethyl)benzonitrile

HRID 1856719Notes

Reaction equation

HRID 1856719 reaction equation
[CH:1]1[C:6]([CH2:7]Br)=[CH:5][CH:4]=[C:3]([C:9]#[N:10])[CH:2]=1.[CH3:11][NH2:12]>C(#N)C>[CH3:11][NH:12][CH2:7][C:6]1[CH:5]=[CH:4][C:3]([C:9]#[N:10])=[CH:2][CH:1]=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 a-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 vacua. Water was added to the residue and extracted 2× with dichloromethane. The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacua 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 vacua to give 1.13 g of pure 4-(methylamino)benzonitrile as a colorless oil.

Workup

  1. concentrationconcentrated in vacua
  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 vacua

Sources & evidence

ORD record
ord-1eac827d4166434b909cde60cb695418
Source dataset
uspto-grants-2000_11
Patent number
US06143760

Reaction notes

Loading…