Ethylamine → Benzonitrile, 3-((ethylamino)methyl)-

HRID 2404315Notes

Reaction equation

HRID 2404315 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7].[CH2:11]([NH2:13])[CH3:12]>C1COCC1>[CH2:11]([NH:13][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7])[CH3:12]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 97249Benzonitrile, 3-(bromomethyl)-

Product 1

HCID 457596Benzonitrile, 3-((ethylamino)methyl)-Yield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(Bromomethyl)benzonitrile (20.0 g, 0.1 mol) was added portion wise into a 2M solution of ethylamine in THF (150 mL) at 0° C. After 5 hours, the reaction mixture was concentrated under vacuum. The residue was taken up with water and extracted with DCM. The organic layer was dried over sodium sulphate and evaporated under reduced pressure to afford the title compound as yellow liquid (12 g, 73%). 1H NMR (DMSO-d6, 400 MHz) δ 7.75 (s, 1H), 7.67 (d, 2H), 7.50 (m, 1H), 3.71 (s, 2H), 2.46 (m, 2H), 0.99 (m, 3H).

Workup

  1. concentrationthe reaction mixture was concentrated under vacuum
  2. extractionextracted with DCM
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8f80384114d84864a544a2a8d47c068e
Source dataset
uspto-grants-2014_08
Patent number
US08802704B2

Reaction notes

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