Benzylamine → 4-(Benzylamino)butanenitrile

HRID 1389203Notes

Reaction equation

HRID 1389203 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:10][CH2:11][CH2:12][C:13]#[N:14].C1CCCCC1.Br.C(N)C1C=CC=CC=1>C(OCC)C>[CH2:1]([NH:8][CH2:10][CH2:11][CH2:12][C:13]#[N:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 8078CyclohexaneHCID 214124-BromobutyronitrileHCID 129985681-Phenylmethanamine--hydrogen bromide (1/1)

Product 1

HCID 30145704-(Benzylamino)butanenitrileYield 66%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

32.2 g of benzylamine, 14.8 g of 4-bromobutyronitrile and 30 ml of cyclohexane are stirred at room temperature for 12 hours. After the addition of diethyl ether the separated benzylamine hydrobromide is filtered off; the ether phase is washed with water, dried and concentrated by evaporation. The residue is distilled in vacuo to yield 11.5 g (66% of theory) of 4-benzylaminobutyronitrile (B.P. 114° to 120°/0.05 mm Hg).

Workup

  1. filtrationis filtered off
  2. washthe ether phase is washed with water
  3. customdried
  4. concentrationconcentrated by evaporation
  5. distillationThe residue is distilled in vacuo

Sources & evidence

ORD record
ord-3d7c63796250464c962ef37264c77f02
Source dataset
uspto-grants-1981_01
Patent number
US04243678

Reaction notes

Loading…