Hydrochloric Acid → N-(2-Aminoethyl)-4-chlorobenzamide hydrochloride

HRID 2255103Notes

Reaction equation

HRID 2255103 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=1.ClC(OCC)=O.[CH2:24]([NH2:27])[CH2:25][NH2:26].Cl>C(Cl)(Cl)Cl>[ClH:8].[NH2:26][CH2:25][CH2:24][NH:27][C:13](=[O:15])[C:12]1[CH:11]=[CH:10][C:9]([Cl:8])=[CH:17][CH:16]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 3301EthylenediamineHCID 63184-Chlorobenzoic AcidHCID 8471TriethylamineHCID 10928Ethyl chloroformate

Product 1

HCID 5702251N-(2-Aminoethyl)-4-chlorobenzamide hydrochlorideYield 85.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

23 ml (0.17 mol) of triethylamine are added dropwise at 0° to a suspension of 23.5 g (0.15 mol) of 4-chlorobenzoic acid and 15 ml (0.16 mol) of ethyl chloroformate in 200 ml of chloroform. After completion of the addition (0.5 hour), the solution obtained is added dropwise at 0° to a solution of 50 ml (0.75 mol) of ethylenediamine in 100 ml of chloroform. After completion of the reaction, 115 ml of concentrated hydrochloric acid are added dropwise at 0°. The acidic mixture is filtered and the neutral constituents remaining are removed by extraction with chloroform. The aqueous phase is then made alkaline with sodium hydroxide solution and extracted several times with chloroform. The chloroform extracts are dried and concentrated. The residue is converted into the hydrochloride which is recrystallized from ethanol/ether. There are obtained 15.1 g of N-(2-aminoethyl)-4-chlorobenzamide hydrochloride, m.p. 212°-214°. The free base melts at 43°-45°.

Workup

  1. additionAfter completion of the addition (0.5 hour)
  2. customthe solution obtained
  3. additionare added dropwise at 0°
  4. filtrationThe acidic mixture is filtered
  5. customthe neutral constituents remaining are removed by extraction with chloroform
  6. extractionextracted several times with chloroform
  7. dry with materialThe chloroform extracts are dried
  8. concentrationconcentrated
  9. customis recrystallized from ethanol/ether

Sources & evidence

ORD record
ord-95309a3c0c924fbc919fd38195174ddf
Source dataset
uspto-grants-1993_08
Patent number
US05238962

Reaction notes

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