2-Bromopropane → HCID 86660609, Verbindung

HRID 717657Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 717657
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][CH2:10][CH2:11][C:12]2[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.C(O[CH:23](OCC)[C:24]1C=CC(CCCNC2C=CC(F)=CC=2)=C[CH:25]=1)C.BrC(C)C.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(Cl)(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH:24]([CH3:25])[CH3:23])[CH2:9][CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([CH:16]=[O:17])=[CH:18][CH:19]=2)=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 66615110N-(3-(4-(Diethoxymethyl)phenyl)propyl)-4-fluorobenzenamineHCID 866606104-(3-(4-Fluorophenylamino)propyl)benzaldehyde

Produkt 1

HCID 86660609HCID 86660609, VerbindungAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 4-(3-(4-fluorophenylamino)propyl)benzaldehyde (0.09 g, 0.35 mmol) [prepared form the product of Step B by stirring in acidifies CHCl3] and 2-bromopropane (0.2 ml) and K2CO3 (0.1 g; 0.73 mmol) was stirred at reflux in anhydrous DMF (5 ml) for 6 h. The solvent was evaporated under reduced pressure and the residue was diluted to 50 ml with EtOAc and washed with H2O. The organic layer separated and dried over MgSO4 and filtered. The filtrate was evaporated to dryness and the residue was purified by FCC(SiO2, hexane/EtOAc), to give the title compound (0.078 g, 83%) as creamy paste. 1H-NMR (CDCl3) 10 (s, 1H); 7.78 (d, 2H, J=8.13 Hz); 7.32 (d, 2H, J=8.07 Hz); 6.93-6.86 (m, 2H); 6.82-6.66 (m, 2H); 3.07 (t, 2H, J=7.5 Hz); 2.71 (t, 2H, J=7.5 Hz); 2.71 (t, 2H, 7.62 Hz); 2.27-2.21 (m, 1H); 1.86-1.83 (m, 1H); 1.08 (d, 6H, J=6.6 Hz).

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was diluted to 50 ml with EtOAc
  3. washwashed with H2O
  4. customThe organic layer separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness
  8. customthe residue was purified by FCC(SiO2, hexane/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-a2f0025702d649f8b1148e3b58c23a92
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09193716B2

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