Ethylenediamine → N-(2-Aminoethyl)-4-chlorobenzamide hydrochloride

HRID 2255109Notes

Reaction equation

HRID 2255109 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[CH2:11]([NH2:14])[CH2:12][NH2:13]>CCOCC>[ClH:1].[NH2:13][CH2:12][CH2:11][NH:14][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 85014-Chlorobenzoyl chloride

Product 1

HCID 5702251N-(2-Aminoethyl)-4-chlorobenzamide hydrochlorideYield 30.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 6.2 ml (0.05 mol) of 4-chlorobenzoyl chloride in 150 ml of ether is added dropwise at -10° over a period of 0.5 hour to a solution of 10 ml (0.15 mol) of ethylenediamine in 150 ml of ether. The mixture is left to warm to room temperature, filtered and the white residue is rinsed twice with ether. After concentrating the ether solution, the residue is acidified with dilute hydrochloric acid and extracted several times with ethyl acetate in order to remove the neutral constituents. The aqueous phase is made alkaline with sodium hydroxide solution and extracted several times with chloroform. After evaporating the chloroform, converting the residue into the hydrochloride and recrystallization from ethanol/ether, there are obtained 1.8 g of N-(2-aminoethyl)-4-chlorobenzamide hydrochloride which is identical with the product obtained in Example 1.

Workup

  1. waitThe mixture is left
  2. filtrationfiltered
  3. washthe white residue is rinsed twice with ether
  4. concentrationAfter concentrating the ether solution
  5. extractionextracted several times with ethyl acetate in order
  6. customto remove the neutral constituents
  7. extractionextracted several times with chloroform
  8. customAfter evaporating the chloroform
  9. custominto the hydrochloride and recrystallization from ethanol/ether, there

Sources & evidence

ORD record
ord-87730b0b2e494be4901dc4d3092e09e7
Source dataset
uspto-grants-1993_08
Patent number
US05238962

Reaction notes

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