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Diethylamine → N-(4-{4-[Diethylcarbamoyl-(3-fluoro-phenyl)-methylene]-piperidin-1-yl}-3-fluoro-phenyl)-2-ethyl-butyramide

HRID 1927620
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1927620
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][C:11](=[C:14]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=3)[C:15]([N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[O:16])[CH2:10][CH2:9]2)=[C:4]([F:29])[CH:3]=1.FC1C=C([N+]([O-])=O)C=CC=1N1C[CH2:44][C:43](=[C:46]([C:49]2C=CC=C(F)C=2)C#N)[CH2:42][CH2:41]1.C(Cl)(C(Cl)=O)=[O:57].N(CC)CC>Br.O>[CH2:18]([N:17]([CH2:20][CH3:21])[C:15]([C:14]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=1)=[C:11]1[CH2:12][CH2:13][N:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][C:44](=[O:57])[CH:43]([CH2:46][CH3:49])[CH2:42][CH3:41])=[CH:3][C:4]=2[F:29])[CH2:9][CH2:10]1)=[O:16])[CH3:19]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8021DiethylamineHCID 65578Oxalyl chlorideHCID 69304055HCID 69304055, VerbindungHCID 69305126[1-(2-Fluoro-4-nitro-phenyl)-piperidin-4-ylidene]-(3-fluoro-phenyl)-acetonitrile

Produkt 1

HCID 58870632N-(4-{4-[Diethylcarbamoyl-(3-fluoro-phenyl)-methylene]-piperidin-1-yl}-3-fluoro-phenyl)-2-ethyl-butyramide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 260Hydrogen BromideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

2-[1-(4-Amino-2-fluoro-phenyl)-piperidin-4-ylidene]-N,N-diethyl-2-(3-fluoro-phenyl)-acetamide. A solution of [1-(2-fluoro-4-nitro-phenyl)-piperidin-4-ylidene]-(3-fluoro-phenyl)-acetonitrile in 48% HBr (75 mL) was stirred at 100° C. for 8 h. The mixture was cooled to rt and diluted with H2O (500 mL). The resulting yellow solid was collected by filtration and dried under vacuum. A mixture of this yellow solid and DMF (0.50 mL) in DCE (100 mL) was treated with (COCl)2 (100 mmol) dropwise and was stirred at rt for 30 min. The mixture was concentrated and dried under vacuum. The residue was diluted with DCE (100 mL) and treated with TEA (2.8 mL, 20 mmol) and Et2NH (1.1 mL, 10 mmol). The reaction mixture was stirred at rt for 4 h, then was washed with H2O (100 mL). The organic layer was separated and concentrated. The residue was dissolved in 1:1 EtOH/EtOAc (100 mL), treated with SnCl2.2H2O (10 g), and heated at 100° C. for 16 h. The mixture was cooled to rt, diluted with ice water (100 mL), basified to pH=9 with NaHCO3, and extracted with EtOAc (3×200 mL). The organic layers were combined, dried (Na2SO4), and concentrated to give the crude title compound.

Aufarbeitung

  1. filtrationThe resulting yellow solid was collected by filtration
  2. customdried under vacuum
  3. additionA mixture of this yellow solid and DMF (0.50 mL) in DCE (100 mL)
  4. concentrationThe mixture was concentrated
  5. customdried under vacuum
  6. additionThe residue was diluted with DCE (100 mL)
  7. stirringThe reaction mixture was stirred at rt for 4 h
  8. washwas washed with H2O (100 mL)
  9. customThe organic layer was separated
  10. concentrationconcentrated
  11. dissolutionThe residue was dissolved in 1:1 EtOH/EtOAc (100 mL)
  12. additiontreated with SnCl2.2H2O (10 g)
  13. temperatureheated at 100° C. for 16 h
  14. temperatureThe mixture was cooled to rt
  15. additiondiluted with ice water (100 mL)
  16. extractionextracted with EtOAc (3×200 mL)
  17. dry with materialdried (Na2SO4)
  18. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d88dcf4043f74951be08cf79e9abd70b
Quelldatensatz
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08183239B2

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