Potassium Carbonate → HCID 68465699, Verbindung

HRID 507206Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 507206
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18](F)[C:17]([N+:21]([O-:23])=[O:22])=[CH:16][C:15]=2[F:24])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[F:31][C:32]([F:43])([F:42])[O:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38][NH2:39])=[CH:36][CH:35]=1>CN(C=O)C.ClCCl.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([NH:39][CH2:38][C:37]3[CH:40]=[CH:41][C:34]([O:33][C:32]([F:31])([F:42])[F:43])=[CH:35][CH:36]=3)[C:17]([N+:21]([O-:23])=[O:22])=[CH:16][C:15]=2[F:24])[CH2:10][CH2:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 5718464-(Trifluoromethoxy)benzylamineHCID 66712179HCID 66712179, Verbindung

Produkt 1

HCID 68465699HCID 68465699, VerbindungAusbeute 80,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

8 g of 4-(2,5-difluoro-4-nitro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (23 mmol) and 3.82 g potassium carbonate (27.65 mmol) were suspended in 80 ml DMF under stirring and then treated dropwise within 10 min with a solution of 5.29 g of 4-trifluoromethoxy-benzylamine (27.65 mmol) in 30 ml DMF. The reaction mixture was then stirred for 48 h at rt, diluted with 500 ml dichloromethane and 1 liter of water. After separation, the organic phase was washed with brine (500 ml). The two aqueous phases were then reextracted with 2×250 ml dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and concentrated in vacuo. The solid residue was stirred with 150 ml heptane/ethylacetate 4:1. After 10 minutes the suspension was diluted with 100 ml heptane, and after additional 10 min stirring, filtered. After drying in vacuo, 9.5 g of 4-[2-fluoro-4-nitro-5-(4-trifluoromethoxy-benzylamino)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester was obtained as a yellow solid (80%). MS(ISP): 515.3 (M+H)+.

Aufarbeitung

  1. stirringThe reaction mixture was then stirred for 48 h at rt
  2. customAfter separation
  3. washthe organic phase was washed with brine (500 ml)
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. stirringThe solid residue was stirred with 150 ml heptane/ethylacetate 4:1
  8. additionAfter 10 minutes the suspension was diluted with 100 ml heptane
  9. stirringafter additional 10 min stirring
  10. filtrationfiltered
  11. customAfter drying in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a858a27689d74628b09e6d5b2e9b1ed9
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786128B2

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