Triethylamine → 4-[4-Nitro-3-(2-phenoxy-acetylamino)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 131205

Reaktionsgleichung

Reaktionsgleichung von HRID 131205
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[C:16]([NH2:23])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[O:24]([CH2:31][C:32](Cl)=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(N(CC)CC)C>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[C:16]([NH:23][C:32](=[O:33])[CH2:31][O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 69703Phenoxyacetyl chlorideHCID 22272542Tert-butyl 4-(3-amino-4-nitrophenyl)piperazine-1-carboxylate

Produkt 1

HCID 684636434-[4-Nitro-3-(2-phenoxy-acetylamino)-phenyl]-piperazine-1-carboxylic acid tert-butyl esterAusbeute 81,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 1 g (3.1 mmol) 4-(3-amino-4-nitro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester, 0.793 g (4.65 mmol) phenoxyacetyl chloride and 2.2 g (21.7 mmol) triethylamine in 20 ml THF was stirred at room temperature for 30 min. The mixture was evaporated and 100 ml DCM were added. The organic phase was washed with 2×50 ml 0.1 M Na2CO3 aq. The combined aqueous phase was extracted with 2×100 ml DCM. The combined organic phases were dried with MgSO4 and evaporated to dryness. The residue was purified over silica eluting with ethyl acetate/hexane 1/1 to yield 1.15 g (81%) of the title compound as yellow solid. MS(ISP): 455.3 (M−H)−.

Aufarbeitung

  1. customThe mixture was evaporated
  2. addition100 ml DCM were added
  3. washThe organic phase was washed with 2×50 ml 0.1 M Na2CO3 aq. The combined aqueous phase
  4. extractionwas extracted with 2×100 ml DCM
  5. dry with materialThe combined organic phases were dried with MgSO4
  6. customevaporated to dryness
  7. customThe residue was purified over silica eluting with ethyl acetate/hexane 1/1

Quellen und Nachweise

ORD-Eintrag
ord-bd6f8070862c4cd49214fc4ab082ceaa
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384945B2

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