N-Methylbenzeneethanamine → HCID 9929893, Verbindung

HRID 1635493Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1635493
Cl[C:2]1[CH:7]=[C:6]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=3)[N:11]=[C:10]([CH3:20])[CH:9]=2)[CH:5]=[CH:4][N:3]=1.[CH3:21][NH:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[CH3:21][N:22]([CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:2]1[CH:7]=[C:6]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=3)[N:11]=[C:10]([CH3:20])[CH:9]=2)[CH:5]=[CH:4][N:3]=1

Komponenten

3

Edukt 2

HCID 11503N-MethylbenzeneethanamineHCID 114829832-chloro-4-[1-(3-methylphenyl)-3-methyl-1H-pyrazol-5-yl]pyridine

Produkt 1

HCID 9929893HCID 9929893, VerbindungAusbeute 67 %

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

A mixture of 2-chloro-4-[1-(3-methylphenyl)-3-methyl-1H-pyrazol-5-yl]pyridine (Example 45; 0.5 g, 0.0018 mol) and N-methylphenethylamine (15 mL) was heated at 200° C. for 24 hours. The excess amine was removed under vacuum and the residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate and filtered. The filtrate was concentrated and the crude was purified by chromatography on silica gel (ethyl acetate/hexane, 2:8) to give 0.45 g (67% yield) of product as a yellow oil: Anal. Calc'd. for C25H26N4: C, 78.50; H, 6.85; N, 14.65. Found: C, 78.43; H, 6.87; N, 14.30.

Aufarbeitung

  1. customThe excess amine was removed under vacuum
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customthe crude was purified by chromatography on silica gel (ethyl acetate/hexane, 2:8)

Quellen und Nachweise

ORD-Eintrag
ord-acf3959637ff4accab8868ca80cb78f9
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06509361B1

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