Hydrochloric Acid → HCID 59458783, compound

HRID 238850Notes

Reaction equation

HRID 238850 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([C:12]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)([N+:20]#[C-])[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:3]=1.Cl>CO.O1CCOCC1>[F:1][C:2]1[CH:3]=[C:4]([C:12]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)([NH2:20])[CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:5]=[C:6]([C:8]([F:10])([F:11])[F:9])[CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59459094HCID 59459094, compound

Product 1

HCID 59458783HCID 59458783, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1-fluoro-3-(1-(4-fluorophenyl)-1-isocyano-2-phenylethyl)-5-(trifluoromethyl)benzene (20 mg, 0.052 mmol) in MeOH (0.4 mL) was added 4 N HCl in dioxane (0.3 mL) and the reaction mixture was stirred for 3 minutes. The reaction solvent was evaporated under a stream of nitrogen. The residue was diluted with 1 N NaOH (5 mL) and the aqueous portion was extracted with Et2O (3×5 mL). The combined organic fractions were washed with sat. NaCl (5 mL), dried over Na2SO4, filtered and evaporated under vacuum to yield 1-(3-fluoro-5-(trifluoromethyl)phenyl)-1-(4-fluorophenyl)-2-phenylethanamine (19 mg, 97% yield) as a clear glass.

Workup

  1. customThe reaction solvent was evaporated under a stream of nitrogen
  2. additionThe residue was diluted with 1 N NaOH (5 mL)
  3. extractionthe aqueous portion was extracted with Et2O (3×5 mL)
  4. washThe combined organic fractions were washed with sat. NaCl (5 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-0bc5ff9772154e25947b56d7ded8c191
Source dataset
uspto-grants-2014_02
Patent number
US08642576B2

Reaction notes

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