Hydrochloric Acid → HCID 86638581, compound

HRID 1807797Notes

Reaction equation

HRID 1807797 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[CH2:21][CH2:20][N:19]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-])=O)[CH:24]=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.ClCCl.C(=O)([O-])[O-].[K+].[K+].[Fe]>[NH2:29][C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][CH:26]=1)[CH2:22][N:19]1[CH2:20][CH2:21][N:16]([CH2:15][C:12]2[CH:11]=[CH:10][C:9]([C:3]([OH:8])([C:2]([F:33])([F:32])[F:1])[C:4]([F:5])([F:6])[F:7])=[CH:14][CH:13]=2)[CH2:17][CH2:18]1

Participants

7

Reactant 2

HCID 313Hydrochloric AcidHCID 86638580HCID 86638580, compound

Product 1

HCID 86638581HCID 86638581, compoundYield 64%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 3776IsopropanolSolventHCID 6344DichloromethaneSolventHCID 11430Potassium CarbonateSolvent

Procedure

To a stirred suspension of 1,1,1,3,3,3-hexafluoro-2-(4-((4-(3-nitrobenzyl)piperazin-1-yl)methyl)phenyl)propan-2-ol (2.095 mmol, 1 g) and iron powder (20.95 mmol, 1.170 g) in 2-propanol was added a small volume of hydrochloric acid (37%). The reaction was refluxed for 2 hours then was allowed to cool to room temperature. The reaction was diluted with dichloromethane and solid potassium carbonate was added. The suspension was stirred for 18 hours then was filtered through celite. The filtrate was concentrated under reduced pressure then was purified by silica chromatography eluting with ethyl acetate to give the title compound (600 mg). MS (ESI) m/z 448.3 [M+H]+

Workup

  1. temperatureThe reaction was refluxed for 2 hours
  2. additionwas added
  3. filtrationthen was filtered through celite
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthen was purified by silica chromatography
  6. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-da488ab80cf94137b461393368e2903e
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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