Hydrochloric Acid → 4-Fluoro-alpha-(4-fluorophenyl)benzenemethanamine

HRID 730430Notes

Reaction equation

HRID 730430 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:16]C=O)[C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.Cl.[OH-].[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[NH2:16])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 25126459N-[Bis(4-fluorophenyl)methyl]formamide

Product 1

HCID 109550394-Fluoro-alpha-(4-fluorophenyl)benzenemethanamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixed solution of bis(4-fluorophenyl)methylformamide (13.9 g, 56.2 mmol), concentrated hydrochloric acid (80 ml) and methanol (160 ml) was stirred at 90° C. for 1.5 hours and cooled to room temperature, then a 6 N aqueous sodium hydroxide solution (170 ml) was added thereto, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to give the objective product as a solid material. Yield (amount) 11.5 g, yield (rate) 93.5%

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-7f54a19e89a546a899f2de2e0d9bdedf
Source dataset
uspto-grants-2009_09
Patent number
US07582651B2

Reaction notes

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