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

HRID 1878342Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1878342
[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

Komponenten

5

Edukt 2

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

Produkt 1

HCID 579176473-((4-(4-Amino-2-fluorobenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamideAusbeute 90,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-4b05fec6881a42cbaef21bb572ced32c
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08314091B2

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