Methylamine → 3-(Methylaminomethyl)benzonitrile

HRID 2404298Notes

Reaction equation

HRID 2404298 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7].[CH3:11][NH2:12]>>[CH3:11][NH:12][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 97249Benzonitrile, 3-(bromomethyl)-

Product 1

HCID 4575953-(Methylaminomethyl)benzonitrileYield 82%

Procedure

To a stirred solution of methylamine (40% in water, 200 mL) under N2, was added 3-(bromomethyl)benzonitrile (10 g, 51 mmol) slowly in portions over 10 minutes at 0° C. After being stirred at RT for 3 hours, the reaction mixture was extracted with DCM. Then the organic layer was washed with brine and dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by chromatography (silica, pet ether/EtOAc) to afford the title compound as a pale yellow liquid (6.1 g, 82%). 1H NMR (DMSO-d6, 400 MHz) δ 7.74 (s, 1H), 7.63-7.68 (m, 2H), 7.48-7.52 (m, 1H), 3.66 (s, 2H), 2.22 (s, 3H).

Workup

  1. extractionthe reaction mixture was extracted with DCM
  2. washThen the organic layer was washed with brine
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by chromatography (silica, pet ether/EtOAc)

Sources & evidence

ORD record
ord-c35e8d4954374455a9521e1cf53258c3
Source dataset
uspto-grants-2014_08
Patent number
US08802704B2

Reaction notes

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