Benzylamine → 4-(4-Benzylamino-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

HRID 1267117Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1267117
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:28][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 3

HCID 7504BenzylamineHCID 23676156Sodium t-butoxideHCID 54371851Tert-butyl 4-(4-bromophenyl)-3,6-dihydropyridine-1(2h)-carboxylate

Produkt 1

HCID 537487374-(4-Benzylamino-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl esterAusbeute 73,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 634876Binap, (A+-)-KatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 4-(4-bromo-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (0.34 g), benzylamine (0.12 g) and sodium tert-butoxide (0.13 g) in toluene (8 mL) were added tris(dibenzylidene acetone)dipalladium (2.2 mg) and Binap (4.6 mg) and the mixture was heated at 80° C. for 16 hours. The solution was then cooled to room temperature, filtered and the filtrate was evaporated under reduced pressure. The residue was purified by flash chromatography eluting with petroleum ether/AcOEt (90/10) and the oily residue was crystallized from diisopropyl ether to give the title compound (0.27 g) as white crystals.

Aufarbeitung

  1. temperatureThe solution was then cooled to room temperature
  2. filtrationfiltered
  3. customthe filtrate was evaporated under reduced pressure
  4. customThe residue was purified by flash chromatography
  5. washeluting with petroleum ether/AcOEt (90/10)
  6. customthe oily residue was crystallized from diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-9c1ca8c990864d51a54fac36ad021f03
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06552022B1

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