Water → (S)-1-(3,4,5-Trifluorophenyl)ethan-1-amine

HRID 1436119Notes

Reaction equation

HRID 1436119 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:20]([C@H:23]([C:25]1[CH:26]=[C:27]([F:33])[C:28]([F:32])=[C:29]([F:31])[CH:30]=1)[CH3:24])=[N+]=[N-].O>C1COCC1>[F:31][C:29]1[CH:30]=[C:25]([C@@H:23]([NH2:20])[CH3:24])[CH:26]=[C:27]([F:33])[C:28]=1[F:32]

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 866126155-((S)-1-azidoethyl)-1,2,3-trifluorobenzene

Product 1

HCID 51358460(S)-1-(3,4,5-Trifluorophenyl)ethan-1-amineYield 46.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triphenylphosphine (1.23 g) was added to a solution of 5-((S)-1-azidoethyl)-1,2,3-trifluorobenzene (858 mg) in THF (20 ml) in a nitrogen atmosphere, and the reaction solution was stirred at room temperature for five minutes. Thereafter, water (2.5 ml) was added to the reaction solution, which was then stirred at 60° C. for 2.5 hours. The reaction solution was returned to room temperature, followed by extraction with 2 N hydrochloric acid (twice). The hydrochloric acid extraction layer was washed with ethyl acetate and then made basic with a 5 N sodium hydroxide solution, followed by extraction with methylene chloride (twice). The methylene chloride layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to obtain 348 mg of the title compound. Further, the following operation was performed in order to collect the title compound remaining in the ethyl acetate dilution of the reaction solution. Diethyl ether was added to the dilution, followed by extraction with water. The water extraction layer was washed with diethyl ether and then made basic with a 5 N sodium hydroxide solution, followed by extraction with methylene chloride (twice). The methylene chloride layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to obtain 413 mg of the title compound.

Workup

  1. stirringwas then stirred at 60° C. for 2.5 hours
  2. customwas returned to room temperature
  3. extractionfollowed by extraction with 2 N hydrochloric acid (twice)
  4. extractionThe hydrochloric acid extraction layer
  5. washwas washed with ethyl acetate
  6. extractionfollowed by extraction with methylene chloride (twice)
  7. dry with materialThe methylene chloride layer was dried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-64f80dfbc92942a0b11281ed60e8a623
Source dataset
uspto-grants-2009_11
Patent number
US07618960B2

Reaction notes

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