Benzylamine → 2-(benzylamino)acetonitrile

HRID 1379986Notes

Reaction equation

HRID 1379986 reaction equation
[CH2:1](O)[C:2]#[N:3].[CH2:5]([NH2:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CO>[CH2:5]([NH:12][CH2:1][C:2]#[N:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 7857Hydroxyacetonitrile

Product 1

HCID 2422122-(benzylamino)acetonitrileYield 65.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of glycollonitrile (25 g) in methanol was added dropwise over 45 minutes benzylamine (46.9 g) keeping the temperature of the reaction between 15°-20°. Following the addition the reaction mixture was kept overnight at room temperature, and then distilled to give benzylaminoacetonitrile (42.0 g) as a colourless oil, b.p. 120°/15 mm. Reaction of this (3.0 g) with 3,5-dimethylbenzoyl chloride (3.46 g) was described above gave crude N-benzyl-3,5-dimethylbenzoylaminoacetonitrile (5.81 g) as a colourless viscous oil which was used in the next stage without further purification. To this crude amide (2.0 g) in anhydrous methylene chloride (8 ml) was added sulphuryl chloride (0.97 g). Following the cessation of gas evolution (ca. 15 min.), anhydrous methanol (20 ml) and finely powdered anhydrous potassium carbonate (1.95 g) was added to the mixture which was then stirred for 30 minutes. Solids were removed from the solution which was then evaporated and the residual oil chromatographed on a column of silica using methylene chloride as an eluent. Following elution from the column and evaporation of the solvent, the product (1.2 g) was obtained as a very pale-yellow viscous oil.

Workup

  1. customthe temperature of the reaction between 15°-20°
  2. additionthe addition the reaction mixture
  3. distillationdistilled

Sources & evidence

ORD record
ord-1a581bda442d4cd29762a3efc837774c
Source dataset
uspto-grants-1986_04
Patent number
US04579581

Reaction notes

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