Triethylamine → N-(3-ethoxycarbonylpropyl)-N-[2-(chroman-3-yl)ethyl]-amine

HRID 1196043Notes

Reaction equation

HRID 1196043 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.[CH2:21]([O:23][C:24](=[O:29])[CH2:25][CH2:26][CH2:27]Br)[CH3:22]>CO>[CH2:21]([O:23][C:24]([CH2:25][CH2:26][CH2:27][NH: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)=[O:29])[CH3:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76300Ethyl 4-bromobutyrateHCID 148384082-(3,4-dihydro-2H-1-benzopyran-3-yl)ethan-1-amine

Product 1

HCID 14838465N-(3-ethoxycarbonylpropyl)-N-[2-(chroman-3-yl)ethyl]-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 19.5 g (0.1 mol) of 4-bromobutyric acid ethyl ester are added to the solution. The reaction mixture is stirred for 15 hours at room temperature and is 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. Oily N-(3-ethoxycarbonylpropyl)-N-[2-(chroman-3-yl)ethyl]-amine is thus obtained and can be used further in crude form.

Workup

  1. concentrationis then concentrated 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-6c382037d0704bc1bbecabd86769aec6
Source dataset
uspto-grants-1992_05
Patent number
US05112855

Reaction notes

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