Methylamine → 3-(Methylaminomethyl)benzonitrile

HRID 219882

Reaktionsgleichung

Reaktionsgleichung von HRID 219882
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]

Komponenten

3

Edukt 2

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

Produkt 1

HCID 4575953-(Methylaminomethyl)benzonitrileAusbeute 82 %

Versuchsvorschrift

To a stirred solution of methylamine (40% in water) (200 mL) under N2, was added 3-(bromomethyl)benzonitrile (10 g, 0.051 mol) slowly in small portions over a period of 10 min at 0° C. After being stirred at RT for 3 h, 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 obtained crude was purified using column chromatography on silica gel (pet ether/ethyl acetate) 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).

Aufarbeitung

  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 obtained crude
  6. customwas purified

Quellen und Nachweise

ORD-Eintrag
ord-0628b36258034376bf59d4f88aa83695
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202865B2

Verknüpfte Notizen

Wird geladen…