Hydrochloric Acid → HCID 69891655, compound

HRID 2416579Notes

Reaction equation

HRID 2416579 reaction equation
C([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)#N.[ClH:12].[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1.C([N:20](CC)CC)C>C(OCC)(=O)C.C(O)C>[ClH:12].[NH:20]=[C:14]1[CH2:15][CH2:16][CH2:17][N:13]1[C:3]1[CH:4]=[CH:5][C:6]([C:7]([OH:9])=[O:8])=[CH:10][CH:11]=1

Participants

7

Reactant 4

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

Product 1

HCID 69891655HCID 69891655, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

15.2 g (103 mmol) of 4-cyanobenzoic acid was added to a mixture of a solution of 4 N hydrogen chloride in 200 ml of ethyl acetate and 50 ml of ethanol, and they were stirred for 5 days. The solvent was evaporated under reduced pressure. 100 ml of ethyl acetate was added to the obtained solid, and they were stirred for 30 minutes. The solid was taken by the filtration. The solid was reacted with 15.0 g (211 mmol) of pyrrolidine and 10.0 g (98.8 mmol) of triethylamine in 100 ml of ethanol as the solvent for two days. The solvent was evaporated. 40 ml of 6 N hydrochloric acid was added to the residue, and they were reacted at 85° C. for 4 hours. The solvent was evaporated, 50 ml of 1 N hydrochloric acid was added to the reaction mixture, and they were stirred for 30 minutes. The solid was taken by the filtration and then washed with 20 ml of ice/water. After the drying under reduced pressure, the title compound was obtained.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. addition100 ml of ethyl acetate was added to the obtained solid, and they
  3. stirringwere stirred for 30 minutes
  4. filtrationThe solid was taken by the filtration
  5. customThe solvent was evaporated
  6. addition40 ml of 6 N hydrochloric acid was added to the residue, and they
  7. customwere reacted at 85° C. for 4 hours
  8. customThe solvent was evaporated
  9. addition50 ml of 1 N hydrochloric acid was added to the reaction mixture, and they
  10. stirringwere stirred for 30 minutes
  11. filtrationThe solid was taken by the filtration
  12. washwashed with 20 ml of ice/water

Sources & evidence

ORD record
ord-921f40fc91994308890c0a28ce238c59
Source dataset
uspto-grants-2004_11
Patent number
US06825181B1

Reaction notes

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