Benzylamine → N-Benzylbis(2-cyanoethyl)amine

HRID 1805772Notes

Reaction equation

HRID 1805772 reaction equation
[C:1](#[N:4])[CH:2]=[CH2:3].[CH2:5]([NH2:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>>[C:1]([CH2:2][CH2:3][N:12]([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:3][CH2:2][C:1]#[N:4])#[N:4]

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 7855Acrylonitrile

Product 1

HCID 11171892N-Benzylbis(2-cyanoethyl)amineYield 93.5%

Conditions

Temperature
70 °C

Procedure

18.58 g of acrylonitrile was added dropwise to an aqueous solution (80 mL) of 10.71 g of benzylamine at room temperature over 1 hour and 20 minutes. Thereafter, the mixture was heated and stirred at 70° C. for 8 hours. After the reaction mixture was concentrated to dryness, 100 mL of water was added thereto, followed by extraction of the mixture with ethyl acetate (150 mL). After the organic layer obtained was washed with water, it was dried with anhydrous magnesium sulfate. The solvent was distilled off to give 19.93 g of the title compound as a colorless oil.

Workup

  1. temperatureThereafter, the mixture was heated
  2. concentrationAfter the reaction mixture was concentrated to dryness, 100 mL of water
  3. additionwas added
  4. extractionfollowed by extraction of the mixture with ethyl acetate (150 mL)
  5. customAfter the organic layer obtained
  6. washwas washed with water, it
  7. dry with materialwas dried with anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-206961a7a37e4de7aa78417249fd656b
Source dataset
uspto-grants-2013_01
Patent number
US08354529B2

Reaction notes

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