N,N-Diethylethylenediamine → N-[2-(diethylamino)ethyl]-4-fluorobenzamide

HRID 1381905Notes

Reaction equation

HRID 1381905 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[CH2:11]([N:13]([CH2:17][CH3:18])[CH2:14][CH2:15][NH2:16])[CH3:12]>O1CCCC1>[CH2:11]([N:13]([CH2:17][CH3:18])[CH2:14][CH2:15][NH:16][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=1)[CH3:12]

Participants

4

Reactant 2

HCID 60993N,N-DiethylethylenediamineHCID 678794-Fluorobenzoyl chloride

Product 1

HCID 14664351N-[2-(diethylamino)ethyl]-4-fluorobenzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Add 24.4 g (0.154 mol) of p-fluorobenzoyl chloride in 100 mL of tetrahydrofuran dropwise to 17.88 g (0.154 mol) of N,N-diethylethylenediamine in 150 mL of tetrahydrofuran at 0° C. Stir at 0° C. for about 2 hr then at room temperature for about 17 hr. Concentrate the resultant solution and treat the residue with 1N NaOH until about pH=10. Extract the resultant solution with methylene chloride (2×100 mL). Dry the extract with Na2SO4 amd evaporate the solvent to give the title compound.

Workup

  1. waitat room temperature for about 17 hr
  2. concentrationConcentrate the resultant solution
  3. additiontreat the residue with 1N NaOH until about pH=10
  4. extractionExtract the resultant solution with methylene chloride (2×100 mL)
  5. customDry the
  6. extractionextract with Na2SO4
  7. customamd evaporate the solvent

Sources & evidence

ORD record
ord-7a859c509a7f424595c72b3867095e77
Source dataset
uspto-grants-1989_02
Patent number
US04804662

Reaction notes

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