Ammonium formate → HCID 14497348, compound

HRID 327782Notes

Reaction equation

HRID 327782 reaction equation
C([N:8]1[CH2:12][CH2:11][CH:10]([CH2:13][O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH3:22])[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].CO>[CH3:22][O:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[O:14][CH2:13][CH:10]1[CH2:11][CH2:12][NH:8][CH2:9]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 14497347HCID 14497347, compound

Product 1

HCID 14497348HCID 14497348, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5.0 g of 10% palladium on activated carbon were added to a solution of 5.0 g (17 mmol) of 1-benzyl-3-(2-methoxyphenoxy)methyl-pyrrolidine and 10.6 g (0.17 mol) of ammonium formate in 300 ml of methanol and the mixture was heated to reflux for 1 hour. After cooling, the solution was separated from the catalyst by filtration and the filtrate was freed from solvent in vacuo. The residue was rendered basic using 1N NaOH and the mixture was extracted using ether. After drying and evaporating, 1.5 g (43%) of the title compound were obtained as an oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1 hour
  3. temperatureAfter cooling
  4. customthe solution was separated from the catalyst by filtration
  5. extractionthe mixture was extracted
  6. customAfter drying
  7. customevaporating

Sources & evidence

ORD record
ord-84463a73fab649aebad9361905e73bd2
Source dataset
uspto-grants-1993_12
Patent number
US05274097

Reaction notes

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