Hydrochloric Acid → HCID 59175857, compound

HRID 1807705Notes

Reaction equation

HRID 1807705 reaction equation
[F:1][C:2]([F:34])([F:33])[C:3]([C:9]1[CH:10]=[C:11]([CH:30]=[CH:31][CH:32]=1)[CH2:12][N:13]1[CH2:18][CH2:17][N:16]([C:19]([C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][CH:22]=2)=[O:20])[CH2:15][CH2:14]1)([OH:8])[C:4]([F:7])([F:6])[F:5].Cl>[Fe].C(O)(C)C>[NH2:27][C:24]1[CH:25]=[CH:26][C:21]([C:19]([N:16]2[CH2:17][CH2:18][N:13]([CH2:12][C:11]3[CH:30]=[CH:31][CH:32]=[C:9]([C:3]([OH:8])([C:2]([F:34])([F:33])[F:1])[C:4]([F:5])([F:6])[F:7])[CH:10]=3)[CH2:14][CH2:15]2)=[O:20])=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59175847HCID 59175847, compound

Product 1

HCID 59175857HCID 59175857, compoundYield 76.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 3776IsopropanolSolvent

Procedure

(4-(3-(1,1,1,3,3,3-Hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazin-1-yl)(4-nitrophenyl)methanone (180 mg, 0.37 mmol), iron powder (205 mg, 3.66 mmol), 1 M hydrochloric acid (549 μL, 0.55 mmol) and isopropanol (10 mL) were stirred together, at ambient temperature, for 2 hours before being filtered and concentrated under vacuum. The residue was treated with strong cation exchange column chromatography and purified by silica chromatography (eluting with a solvent gradient from dichloromethane to 4% methanol/dichloromethane). The product was recrystallised from benzonitrile to afford the title compound (131 mg). MS (ESI) m/z 462.1 [M+H]+

Workup

  1. filtrationbefore being filtered
  2. concentrationconcentrated under vacuum
  3. additionThe residue was treated with strong cation exchange column chromatography
  4. custompurified by silica chromatography (
  5. washeluting with a solvent gradient from dichloromethane to 4% methanol/dichloromethane)
  6. customThe product was recrystallised from benzonitrile

Sources & evidence

ORD record
ord-2ee4c0cc70f4447db79ba18b0abfb272
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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