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

HRID 1196036Notes

Reaction equation

HRID 1196036 reaction equation
Cl.[O:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH:4]([CH2:12][CH2:13][NH:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH2:3]1.C(N(CC)CC)C.[C:28](#[N:31])[CH:29]=[CH2:30]>CO>[O:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH:4]([CH2:12][CH2:13][N:14]([CH2:30][CH2:29][C:28]#[N:31])[CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH2:3]1

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 8471TriethylamineHCID 14838449N-[2-(chroman-3-yl)ethyl]-N-(2-methoxycarbonylethyl)-amine hydrochloride

Product 1

HCID 14838450N-[2-(chroman-3-yl)ethyl]-N-(2-cyanoethyl)-N-(2-methoxycarbonylethyl)amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

30 g (0.1 mol) of N-[2-(chroman-3-yl)ethyl]-N-(2-methoxycarbonylethyl)-amine hydrochloride 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 and the whole is stirred for 15 hours at room temperature. The reaction mixture is then concentrated under a water-jet vacuum, the residue is taken up in diethyl ether and the ethereal solution is 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)-N-(2-methoxycarbonylethyl)-amine is thus obtained in the form of a yellow oil.

Workup

  1. concentrationThe reaction mixture is then concentrated under a water-jet vacuum
  2. washthe ethereal solution is washed neutral with ice-water
  3. dry with materialThe ethereal phase is dried over potassium carbonate
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-3808efa6fb6b4c60a92bdbca41bc7118
Source dataset
uspto-grants-1992_05
Patent number
US05112855

Reaction notes

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