Phenethylamine → HCID 9864086, Verbindung

HRID 1635492Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1635492
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.[CH2:21]([NH2:29])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[C:23]1([CH2:22][CH2:21][NH:29][C:2]2[CH:7]=[C:6]([C:8]3[N:12]([C:13]4[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=4)[N:11]=[C:10]([CH3:20])[CH:9]=3)[CH:5]=[CH:4][N:3]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Komponenten

3

Edukt 2

HCID 1001PhenethylamineHCID 114829832-chloro-4-[1-(3-methylphenyl)-3-methyl-1H-pyrazol-5-yl]pyridine

Produkt 1

HCID 9864086HCID 9864086, VerbindungAusbeute 74 %

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 phenethylamine (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, 1:1) to give 0.48 g (74% yield) of product as a yellow oil, which solidified upon standing: mp: 86-87° C. Anal. Calc'd. for C24H24N4: C, 78.23; H, 6.56; N, 15.20. Found: C, 78.07; H, 6.82; N, 14.71.

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, 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-1f6a8b56bb5c41439700bfd9a2bd4f59
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06509361B1

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