Ammonia → 4-(2-Fluorophenoxy)benzenemethanamine

HRID 911256Notes

Reaction equation

HRID 911256 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[O:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1.C(O)C.N>CO.[Ni]>[F:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH2:10])=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 702EthanolHCID 28411324HCID 28411324, compound

Product 1

HCID 195767144-(2-Fluorophenoxy)benzenemethanamineYield 79%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Add 4-(2′-fluorophenoxy)-benzonitrile (1.5 g, 7.0 mmol) and ethanol wet Raney® activated nickel (0.4 g) to a Parr pressure vessel. Immediately add a 7N solution of ammonia in methanol (170 mL) and seal the vessel. Purge the reaction vessel with nitrogen, pressurize the reaction mixture with hydrogen (3400 KPa), seal the vessel, agitate the reaction and heat to 60° C. Continue the reaction for 18 h, turn off the heat and allow the reaction mixture to cool to ambient temperature. Vent the excess hydrogen from the vessel and purge the vessel with nitrogen. Filter the reaction mixture to remove the Raney® nickel. Concentrate in vacuo and purify by chromatography on silica gel eluting with DCM/2M ammonia in methanol (9:1) to obtain the title compound (1.2 g, 79%). MS (ES+) m/z: 201 M+H−NH3)+.

Workup

  1. customseal the vessel
  2. customPurge the reaction vessel with nitrogen
  3. customseal the vessel
  4. customthe reaction
  5. customthe reaction for 18 h
  6. temperatureheat
  7. temperatureto cool to ambient temperature
  8. customVent the excess hydrogen from the vessel and purge the vessel with nitrogen
  9. filtrationFilter the reaction mixture
  10. customto remove the Raney® nickel
  11. concentrationConcentrate in vacuo
  12. custompurify by chromatography on silica gel eluting with DCM/2M ammonia in methanol (9:1)

Sources & evidence

ORD record
ord-612c8a4f226b43ecb83786ee03542b91
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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