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

HRID 1878342Notes

Reaction equation

HRID 1878342 reaction equation
[C:1]([NH:5][C:6](=[O:32])[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)=[CH:23][C:22]=3[F:30])[CH2:16][CH2:15]2)[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].Cl>CC(O)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:32])[CH2:15][CH2:16]2)=[O:31])=[C:22]([F:30])[CH:23]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57917650N-tert-Butyl-3-((4-(2-fluoro-4-nitrobenzoyl)piperazin-1-yl)methyl)benzamide

Product 1

HCID 579176473-((4-(4-Amino-2-fluorobenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamideYield 90.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 3776IsopropanolSolvent

Procedure

To a suspension of iron (O) powder (3.3 g, 58.76 mmol) and N-tert butyl-3-((4-(2-fluoro-4-nitrobenzoyl)piperazin-1-yl)methyl)benzamide (2.6 g, 5.88 mmol) in propan-2-ol (75 mL) was added 1M aqueous hydrochloric acid (8.8 mL, 8.1 mmol). The reaction was stirred at room temperature for 2.5 hours, filtered through dicalite and concentrated under vacuum. The residue was dissolved in methanol and purified by strong cation exchange chromatography, eluting macroporous polystyrene sulfonic acid with 2M ammonia in methanol. The resulting solution was concentrated under vacuum to afford the title compound as a viscous orange oil (2.2 g).

Workup

  1. filtrationfiltered through dicalite
  2. concentrationconcentrated under vacuum
  3. dissolutionThe residue was dissolved in methanol
  4. custompurified by strong cation exchange chromatography
  5. washeluting macroporous polystyrene sulfonic acid with 2M ammonia in methanol
  6. concentrationThe resulting solution was concentrated under vacuum

Sources & evidence

ORD record
ord-4b05fec6881a42cbaef21bb572ced32c
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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