Methylamine → 3-(Methylaminomethyl)benzonitrile

HRID 572580

Reaction equation

HRID 572580 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]>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]

Participants

4

Reactant 2

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

Product 1

HCID 4575953-(Methylaminomethyl)benzonitrileYield 101.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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)+.

Workup

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

Sources & evidence

ORD record
ord-b1a5c3e5b3f447bd9822a05a848b0281
Source dataset
uspto-grants-2015_05
Patent number
US09029405B2

Linked notes

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