Hydrochloric Acid → 3-((4-(4-Amino-3-fluorobenzoyl)-2-(fluoromethyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide

HRID 1878391Notes

Reaction equation

HRID 1878391 reaction equation
[C:1]([NH:5][C:6](=[O:34])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][N:14]2[CH2:19][CH2:18][N:17]([C:20](=[O:31])[C:21]3[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[C:23]([F:30])[CH:22]=3)[CH2:16][CH:15]2[CH2:32][F:33])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].Cl>C(O)(C)C.[Fe]>[NH2:27][C:24]1[CH:25]=[CH:26][C:21]([C:20]([N:17]2[CH2:18][CH2:19][N:14]([CH2:13][C:9]3[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=3)[C:6]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:34])[CH:15]([CH2:32][F:33])[CH2:16]2)=[O:31])=[CH:22][C:23]=1[F:30]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57917722N-tert-Butyl-3-((4-(3-fluoro-4-nitrobenzoyl)-2-(fluoromethyl)piperazin-1-yl)methyl)benzamide

Product 1

HCID 579176673-((4-(4-Amino-3-fluorobenzoyl)-2-(fluoromethyl)piperazin-1-yl)methyl)-N-tert-butylbenzamideYield 36.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 3776IsopropanolSolvent

Procedure

N-tert-butyl-3-((4-(3-fluoro-4-nitrobenzoyl)-2-(fluoromethyl)piperazin-1-yl)methyl)benzamide (435 mg, 0.92 mmol), iron powder (558 mg, 10 mmol) and 1M hydrochloric acid (1.5 mL, 1.5 mmol) were stirred in isopropyl alcohol (30 mL) for 1 hour. The reaction was concentrated under reduced pressure and the residue partitioned between dichloromethane and water. The organic layer was separated, dried (sodium sulfate) and concentrated under reduced pressure. The crude product was purified using silica chromatography to give the title compound (150 mg). MS (ESI) m/z 445.6 [M+H]+

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customthe residue partitioned between dichloromethane and water
  3. customThe organic layer was separated
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified

Sources & evidence

ORD record
ord-8e358582276a4fdea86655c61855ca1a
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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