Acrylonitrile → N-[2-(chroman-3-yl)ethyl]-N-(2-cyanoethyl)-amine

HRID 1032422Notes

Reaction equation

HRID 1032422 reaction equation
[NH2:1][CH2:2][CH2:3][CH:4]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[O:6][CH2:5]1.C(N(CC)CC)C.[C:21](#[N:24])[CH:22]=[CH2:23]>CO>[O:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:13][CH:4]([CH2:3][CH2:2][NH:1][CH2:23][CH2:22][C:21]#[N:24])[CH2:5]1

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 8471TriethylamineHCID 148384082-(3,4-dihydro-2H-1-benzopyran-3-yl)ethan-1-amine

Product 1

HCID 15027461N-[2-(chroman-3-yl)ethyl]-N-(2-cyanoethyl)-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

17.7 g (0.1 mol) of 3-(2-aminoethyl)chroman are dissolved in 100 ml of methanol, and then 10.5 g (0.1 mol) of triethylamine and 5.84 g (0.11 mol) of acrylonitrile are added to the solution. The reaction mixture is stirred for 15 hours at room temperature and then concentrated under a water-jet vacuum. The residue is taken up in diethyl ether and washed neutral with ice-water. The ethereal phase is dried over potassium carbonate and concentrated by evaporation. N-[2-(chroman-3-yl)ethyl]-N-(2-cyanoethyl)-amine is thus obtained in the form of a pale yellow oil.

Workup

  1. concentrationconcentrated under a water-jet vacuum
  2. washwashed neutral with ice-water
  3. dry with materialThe ethereal phase is dried over potassium carbonate
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-4a6c068213d14f8eb6acedd470df7623
Source dataset
uspto-grants-1990_09
Patent number
US04957928

Reaction notes

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