Benzoic Acid → N-(2-Aminoethyl)benzamide--hydrogen chloride (1/1)

HRID 2255106Notes

Reaction equation

HRID 2255106 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:17]C(OCC)=O.[CH2:23]([NH2:26])[CH2:24][NH2:25]>C(Cl)(Cl)Cl>[ClH:17].[NH2:25][CH2:24][CH2:23][NH:26][C:1](=[O:9])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 3301EthylenediamineHCID 8471TriethylamineHCID 10928Ethyl chloroformate

Product 1

HCID 12715873N-(2-Aminoethyl)benzamide--hydrogen chloride (1/1)

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

24.4 g (0.02 mol) of benzoic acid are reacted with triethylamine and ethyl chloroformate in a manner analogous to that described in Example 5 and added dropwise at 10° to a solution of 53.5 ml (0.8 mol) of ethylenediamine in 750 ml of chloroform. After removing the difficulty soluble neutral constituents by filtration, the chloroform solution is concentrated and excess ethylenediamine is removed in a high vacuum. The oily residue (36.3 g) is taken up in 200 ml of 2N sodium hydroxide solution, saturated with solid sodium chloride and extracted several times with ethyl acetate. The ethyl acetate extracts are dried over magnesium sulfate and concentrated. The product is converted into the hydrochloride which is purified by recrystallization from ethanol, there being obtained 5.2 g of N-(2- aminoethyl)benzamide hydrochloride [J. Amer. Chem. Soc. 61, 822 (1939)], m.p. 163°-165°.

Workup

  1. customAfter removing the difficulty soluble neutral constituents
  2. filtrationby filtration
  3. concentrationthe chloroform solution is concentrated
  4. customexcess ethylenediamine is removed in a high vacuum
  5. extractionextracted several times with ethyl acetate
  6. dry with materialThe ethyl acetate extracts are dried over magnesium sulfate
  7. concentrationconcentrated
  8. customis purified by recrystallization from ethanol, there

Sources & evidence

ORD record
ord-08ee53e67ff54b3a854e411a11cf780b
Source dataset
uspto-grants-1993_08
Patent number
US05238962

Reaction notes

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