Hydrochloric Acid → HCID 178478772, compound

HRID 609557Notes

Reaction equation

HRID 609557 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[NH:12])[CH:7]=[CH:8][CH:9]=1)([O-])=O.[H][H].[ClH:20]>[Pd]>[ClH:20].[ClH:20].[NH2:1][C:4]1[CH:5]=[C:6]([NH:10][C:11]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[NH:12])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 178418361HCID 178418361, compoundHCID 178512041HCID 178512041, compound

Product 1

HCID 178478772HCID 178478772, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A sample of the product of step (a), 17 g, was dissolved in 200 ml of 1 M hydrochloric acid. The mixture was then hydrogenated with 1 g of 5% Pd/C. When hydrogen uptake had stopped the catalyst was filtered off. The solvent was evaporated in vacuum, and the residue dissolved in isopropanol, evaporated in vacuum again and the residue dissolved in 100 ml of methanol. To this mix was added 200 ml of toluene. This was then concentrated on a steam bath until the volume had decreased to approximately 175 ml. The crystals that precipitated were filtered to give N-(3-aminophenyl)-1-pyrrolidinecarboximidamide dihydrochloride, m.p. 250-251° C.

Workup

  1. filtrationwas filtered off
  2. customThe solvent was evaporated in vacuum
  3. dissolutionthe residue dissolved in isopropanol
  4. customevaporated in vacuum again
  5. dissolutionthe residue dissolved in 100 ml of methanol
  6. additionTo this mix was added 200 ml of toluene
  7. concentrationThis was then concentrated on a steam bath until the volume
  8. customThe crystals that precipitated
  9. filtrationwere filtered

Sources & evidence

ORD record
ord-fdf92bd609684cd8beed86177bfeefbf
Source dataset
uspto-grants-1999_12
Patent number
US05998399

Reaction notes

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