Ammonium formate → HCID 54568336, compound

HRID 429843Notes

Reaction equation

HRID 429843 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([NH:11][C:12]2[CH:13]=[C:14]([CH2:18][C@H:19]([N:21]([C@@H](C3C=CC=CC=3)C)[CH2:22][CH2:23][CH3:24])[CH3:20])[CH:15]=[CH:16][CH:17]=2)=[O:10])=[CH:5][CH:4]=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([NH:11][C:12]2[CH:13]=[C:14]([CH2:18][C@H:19]([NH:21][CH2:22][CH2:23][CH3:24])[CH3:20])[CH:15]=[CH:16][CH:17]=2)=[O:10])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 54387039HCID 54387039, compound

Product 1

HCID 54568336HCID 54568336, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(R,R)-N-{2-[3-(4-methoxyphenylcarbonylamino)phenyl]-1-methylethyl}-N-propyl-(1-phenylethyl)amine (0.98 g) was dissolved in ethanol (100 ml) and added to 10% palladium on carbon (0.1 g). To this mixture was added ammonium formate (1.2 g), and the mixture heated at reflux for 2 hours, cooled to room temperature, and filtered. The filtrate was evaporated in vacuo, and the residue was partitioned between ethyl acetate and dilute sodium hydroxide. The organic layer was dried over sodium sulfate, filtered, and the solvent removed in vacuo to give [(R)-N-{2-[3-(4-methoxyphenylcarbonylamino)phenyl]-1-methylethyl}propylamine.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 2 hours
  3. filtrationfiltered
  4. customThe filtrate was evaporated in vacuo
  5. customthe residue was partitioned between ethyl acetate and dilute sodium hydroxide
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-542800a70f8d41a5a396de36f419d421
Source dataset
uspto-grants-2001_11
Patent number
US06319920B1

Reaction notes

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