1,2-Dibromoethane → N-(3-ethoxycarbonylpropyl)-N-(2-bromoethyl)-N-[2-(chroman-3-yl)ethyl]amine

HRID 1032425Notes

Reaction equation

HRID 1032425 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][CH2:7][CH2:8][NH:9][CH2:10][CH2:11][CH:12]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[O:14][CH2:13]1)=[O:5])[CH3:2].C(N(CC)CC)C.[Br:29][CH2:30][CH2:31]Br>CO>[CH2:1]([O:3][C:4]([CH2:6][CH2:7][CH2:8][N:9]([CH2:31][CH2:30][Br:29])[CH2:10][CH2:11][CH:12]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[O:14][CH2:13]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 8471TriethylamineHCID 14838465N-(3-ethoxycarbonylpropyl)-N-[2-(chroman-3-yl)ethyl]-amine

Product 1

HCID 14838456N-(3-ethoxycarbonylpropyl)-N-(2-bromoethyl)-N-[2-(chroman-3-yl)ethyl]amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

29.1 g (0.1 mol) of N-(3-ethoxycarbonylpropyl)-N-[2-(chroman-3-yl)ethyl]-amine are dissolved in 200 ml of methanol, and then 10.5 g (0.1 mol) of triethylamine and 18.8 g (0.1 mol) of 1,2-dibromoethane are added to the solution. The reaction mixture is stirred for 16 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-(3-ethoxycarbonylpropyl)-N-(2-bromoethyl)-N-[2-(chroman-3-yl)ethyl]amine is thus obtained in the form of an oil which can be used further in the crude state.

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-1ee38fbd93924f0995ef47649dda00ab
Source dataset
uspto-grants-1990_09
Patent number
US04957928

Reaction notes

Loading…