Hydrochloric Acid → HCID 66725981, compound

HRID 2090547Notes

Reaction equation

HRID 2090547 reaction equation
[N:1]([CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20](=[O:25])[CH2:21][N:22]=[N+]=[N-])=[CH:16][CH:15]=2)[CH:8]=1)=[O:6])=[N+]=[N-].[ClH:26]>CO.[Pd]>[ClH:26].[ClH:26].[NH2:1][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][C:14]2[CH:15]=[CH:16][C:17]([C:20](=[O:25])[CH2:21][NH2:22])=[CH:18][CH:19]=2)[CH:8]=1)=[O:6]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58079232HCID 58079232, compound

Product 1

HCID 66725981HCID 66725981, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-azido-1-(3-(4-(2-azidoacetyl)phenoxy)phenyl)ethanone (9 g, 26.4 mmol) in methanol (400 mL) was added HCl (1M in methanol, 53 mL) and the mixture was hydrogenated using Pd/C (10%) under hydrogen atmosphere (1 bar) during 2 hours. The solution was filtered over celite and concentrated under reduced pressure. The crude was dissolved in dichloromethane and after addition of HCl (6N in isopropanol) the hydrochloride salt precipitated. Filtration and drying in vacuo afforded 2-amino-1-(3-(4-(2-aminoacetyl)phenoxy)phenyl)ethanone dihydrochloride.

Workup

  1. customduring 2 hours
  2. filtrationThe solution was filtered over celite and
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe crude was dissolved in dichloromethane
  5. additionafter addition of HCl (6N in isopropanol) the hydrochloride salt
  6. customprecipitated
  7. filtrationFiltration
  8. customdrying in vacuo

Sources & evidence

ORD record
ord-fe78a2f8c95e426f914cad5bf82857f9
Source dataset
uspto-grants-2013_05
Patent number
US08436036B2

Reaction notes

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