Benzylamine → 2-(benzylamino)acetonitrile

HRID 1842713Notes

Reaction equation

HRID 1842713 reaction equation
Cl[CH2:2][C:3]#[N:4].[CH2:5]([NH2:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CCOC(C)=O>[CH2:5]([NH:12][CH2:2][C:3]#[N:4])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 7856Chloroacetonitrile

Product 1

HCID 2422122-(benzylamino)acetonitrileYield 99%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

A solution of the ClCH2CN (316 g, 4.19 mol) in EtOAc (200 mL) was added dropwise to benzylamine (900 g, 8.40 mol) while the mixture was vigorously stirred. The mixture was warmed gently to 45° C. for 0.5 h and a white precipitate was removed by filtration. The filtrate was concentrated in vacuo to give the title compound (606 g, 99%) as yellow oil; 1H NMR: (CDCl3) 3.56 (2H, s), 3.94 (2H, s), 7.28-7.40 (5H, m).

Workup

  1. customa white precipitate was removed by filtration
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-33616c4353f142e9b20366ced7b42224
Source dataset
uspto-grants-2015_02
Patent number
US08946235B2

Reaction notes

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