Dicyclohexylcarbodiimide → Desethyl-N-acetylprocainamide

HRID 1456902Notes

Reaction equation

HRID 1456902 reaction equation
[C:1]([NH:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].O[N:15]1[C:19](=O)[CH2:18][CH2:17][C:16]1=O.C1([N:28]=C=NC2CCCCC2)CCCCC1>N1C=CC=CC=1>[CH3:17][CH2:16][NH:15][CH2:19][CH2:18][NH:28][C:9]([C:8]1[CH:7]=[CH:6][C:5]([NH:4][C:1]([CH3:2])=[O:3])=[CH:13][CH:12]=1)=[O:11]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 19266p-Acetamidobenzoic acidHCID 80170N-Hydroxysuccinimide

Product 1

HCID 155689Desethyl-N-acetylprocainamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
4 °C

Procedure

Desethyl-N-acetylprocainamide was prepared by dissolving 1.0 g of p-acetamidobenzoic acid and 0.7 g N-hydroxysuccinimide in 20 ml pyridine. To this solution was added 1.4 g of N,N'-dicyclohexylcarbodiimide. The reaction mixture was placed at 4° C. for 18 hours, at which time the crystals were removed by filtration. The filtration was brought to room temperature and with stirring, 0.51 g N-ethylethylenediamine ethylethylenediamine was added. Stirring continued for 3 hours, the solution was cooled to 4° C. and allowed to react for an addition 24 hours at 4° C. The second crop of crystals was removed by filtration, dissolved in 25 ml of distilled water. The pH was adjusted to 10 with sodium hydroxide to form a white precipitate of desethyl-N-acetylprocainamide. The resultant precipitate was dried in vacuo and stored at -20° C. in a desiccator.

Workup

  1. customDesethyl-N-acetylprocainamide was prepared
  2. customthe crystals were removed by filtration
  3. filtrationThe filtration
  4. customwas brought to room temperature
  5. addition0.51 g N-ethylethylenediamine ethylethylenediamine was added
  6. stirringStirring
  7. waitcontinued for 3 hours
  8. customto react for an addition 24 hours at 4° C
  9. customThe second crop of crystals was removed by filtration
  10. dissolutiondissolved in 25 ml of distilled water

Sources & evidence

ORD record
ord-524267702cba4f42a4284ce17ea11779
Source dataset
uspto-grants-1998_12
Patent number
US05846703

Reaction notes

Loading…