Ammonium formate → Azetidin-3-yl-(2-methoxy-phenyl-amine)

HRID 1066901Notes

Reaction equation

HRID 1066901 reaction equation
C([N:14]1[CH2:17][CH:16]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25][CH3:26])[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[NH:14]1[CH2:15][CH:16]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25][CH3:26])[CH2:17]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 15521970(1-Benzhydryl-azetidin-3-yl)-(2-methoxyphenyl)-amine

Product 1

HCID 15521971Azetidin-3-yl-(2-methoxy-phenyl-amine)Yield 81.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A solution of 2.0 g of (1-benzhydryl-azetidin-3-yl)-(2-methoxyphenyl)-amine in 30 mL of methanol was added to a suspension of 10% Pd/C in methanol. 4.0 g of ammonium formate was added portion wise and the reaction was heated under reflux for 2 h. The mixture was cooled, filtered over celite, the filtrate was evaporated. The residue was triturated with CH2Cl2, and filtered. The filtrate was evaporated to give 0.840 g of the desired product.

Workup

  1. temperaturethe reaction was heated
  2. temperatureunder reflux for 2 h
  3. temperatureThe mixture was cooled
  4. filtrationfiltered over celite
  5. customthe filtrate was evaporated
  6. customThe residue was triturated with CH2Cl2
  7. filtrationfiltered
  8. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-af7c098eb3264086ba2b1f33ff3a1901
Source dataset
uspto-grants-2001_06
Patent number
US06245799B1

Reaction notes

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