Hydrochloric Acid → HCID 68592844, compound

HRID 747794Notes

Reaction equation

HRID 747794 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)#[N:2].[ClH:12].[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1.C(N(CC)CC)C>C(O)C.C(OCC)(=O)C>[ClH:12].[NH:2]=[C:1]([N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 120874-Cyanobenzoic acidHCID 31268Pyrrolidine

Product 1

HCID 68592844HCID 68592844, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

15.2 g (103 mmol) of 4-cyano-benzoic acid was added to 200 ml of an ethyl acetate solution containing 4 N hydrogen chloride and 50 ml of ethanol, and they were stirred for 5 days. The solvent was distilled off under reduced pressure, and 100 ml of ethyl acetate was added to the resulting solid, and the mixture was stirred for 30 minutes, and the solid was collected by filtration. The resulting solid was reacted with 15.0 g (211 mmol) of pyrrolidine and 10.0 g (98.8 mmol) of triethylamine for 2 days in 100 ml ethanol as the solvent. The solvent was distilled off, and 40 ml of 6 N hydrochloric acid was added to the residue, and it was reacted at 85° C. for 4 hours. The solvent was distilled off, and 50 ml of 1 N hydrochloric acid was added to the residue which was then stilled for 30 minutes, and the solid was collected by filtration and washed with 20 ml of ice-cold water. It was dried under reduced pressure to obtain the title compound.

Workup

  1. distillationThe solvent was distilled off under reduced pressure, and 100 ml of ethyl acetate
  2. additionwas added to the resulting solid
  3. stirringthe mixture was stirred for 30 minutes
  4. filtrationthe solid was collected by filtration
  5. distillationThe solvent was distilled off
  6. addition40 ml of 6 N hydrochloric acid was added to the residue, and it
  7. customwas reacted at 85° C. for 4 hours
  8. distillationThe solvent was distilled off
  9. addition50 ml of 1 N hydrochloric acid was added to the residue which
  10. waitwas then stilled for 30 minutes
  11. filtrationthe solid was collected by filtration
  12. washwashed with 20 ml of ice-cold water
  13. customIt was dried under reduced pressure

Sources & evidence

ORD record
ord-663c14172b1043b8a323c39a03480d24
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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