Hydrochloric Acid → HCID 86638576, compound

HRID 1807787Notes

Reaction equation

HRID 1807787 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[CH:26][C:25]([N+:28]([O-])=O)=[CH:24][CH:23]=3)[CH2:18][CH2:17]2)=[CH:11][CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].Cl>CC(O)C.CCOCC.[Fe]>[NH2:28][C:25]1[CH:24]=[CH:23][C:22]([N:19]2[CH2:18][CH2:17][N:16]([CH2:15][C:12]3[CH:11]=[CH:10][C:9]([C:3]([OH:8])([C:2]([F:32])([F:31])[F:1])[C:4]([F:5])([F:6])[F:7])=[CH:14][CH:13]=3)[CH2:21][CH2:20]2)=[CH:27][CH:26]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 86638575HCID 86638575, compound

Product 1

HCID 86638576HCID 86638576, compoundYield 50.8%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolvent

Procedure

To a stirred mixture of 1,1,1,3,3,3-hexafluoro-2-(4-((4-(4-nitrophenyl)piperazin-1-yl)methyl)phenyl)propan-2-ol (17.26 mmol, 8 g) and iron (143 mmol, 8 g) in 2-propanol was added 2M hydrochloric acid. The reaction was refluxed for 3 hours. The reaction was filtered through celite washing with 2-propanol and concentrated under reduced pressure. Water and ethyl acetate was added. Solid potassium carbonate was added until the aqueous layer was basic. The organic phase was separated and the water layer was extracted with dichloromethane. The combined organic phases were combined, dried (sodium sulfate) and concentrated under reduced pressure. The crude material was chromatographed on silica eluting with ethyl acetate. The brown solid obtained was stirred in ether and filtered to give the title compound (3.8 g). MS (ESI) m/z 434.1 [M+H]+

Workup

  1. temperatureThe reaction was refluxed for 3 hours
  2. filtrationThe reaction was filtered
  3. washthrough celite washing with 2-propanol
  4. concentrationconcentrated under reduced pressure
  5. additionWater and ethyl acetate was added
  6. additionSolid potassium carbonate was added until the aqueous layer
  7. customThe organic phase was separated
  8. extractionthe water layer was extracted with dichloromethane
  9. dry with materialdried (sodium sulfate)
  10. concentrationconcentrated under reduced pressure
  11. customThe crude material was chromatographed on silica eluting with ethyl acetate
  12. customThe brown solid obtained
  13. filtrationfiltered

Sources & evidence

ORD record
ord-d8f8c7d78f4445ad96d49d8dc34f8ace
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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