Methylamine → 3-(Methylaminomethyl)benzonitrile

HRID 572580

Reaktionsgleichung

Reaktionsgleichung von HRID 572580
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]>C1COCC1>[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

4

Edukt 2

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

Produkt 1

HCID 4575953-(Methylaminomethyl)benzonitrileAusbeute 101,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In a 3 necked round bottom flask (250 ml), put under nitrogen atmosphere, a solution of 3-(bromomethyl)benzonitrile (5 g; 25.5 mmol; 1 eq.) in anhydrous THF (20 ml) was added dropwise into methylamine (63.76 ml; 2 M; 127.52 mmol; 5 eq.) (2M solution in THF) over 1 hour. The reaction mixture was stirred at RT for 2 hours. Some bis-benzylation was observed (7%). The reaction mixture was filtered to remove the salt. The filtrate was evaporated under reduced pressure. The residue was taken up with DCM and evaporated again to give the title compound as a yellow oil (3.78 g, quantitative yield). It was used in the next step without any further purification. LC/MS (Method B) 146.8 (M+H)+.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. customto remove the salt
  3. customThe filtrate was evaporated under reduced pressure
  4. customevaporated again

Quellen und Nachweise

ORD-Eintrag
ord-b1a5c3e5b3f447bd9822a05a848b0281
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029405B2

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