Ethylenediamine → N-(2-aminoethyl)-4-fluorobenzamide

HRID 2255111Notes

Reaction equation

HRID 2255111 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=O)=[CH:4][CH:3]=1.[CH2:12]([NH2:15])[CH2:13][NH2:14]>>[NH2:14][CH2:13][CH2:12][NH:15][C:6](=[O:8])[C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 67878Methyl 4-fluorobenzoate

Product 1

HCID 5203773N-(2-aminoethyl)-4-fluorobenzamide

Procedure

7.7 g (0.05 mol) of methyl 4-fluorobenzoate and 10 ml (0.15 mol) of ethylene diamine are heated to 130° (bath temperature) for 2 hours. The mixture is poured on to ice/hydrochloric acid and extracted 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 drying and concentrating the chloroform extracts, the residue (7.6 g) is recrystallized from ethyl acetate/hexane, the being obtained N-(2-aminoethyl)-4-fluorobenzamide, m.p. 57°-60°. The hydrochloride melts at 214°-216°.

Workup

  1. extractionextracted with ethyl acetate in order
  2. customto remove the neutral constituents
  3. extractionextracted several times with chloroform
  4. customAfter drying
  5. concentrationconcentrating the chloroform
  6. customthe residue (7.6 g) is recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-c04c7d4805b04070ba30bb15d4416f02
Source dataset
uspto-grants-1993_08
Patent number
US05238962

Reaction notes

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