Phenethylamine → Benzyl-[8-(4-benzyl-piperazin-1-yl)-quinolin-6-yl]-methyamine

HRID 428547

Reaktionsgleichung

Reaktionsgleichung von HRID 428547
C([O-])([O-])=O.[Cs+].[Cs+].C1C=CC(P([C:20]2[C:29]([C:30]3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=[C:28]3[C:23](C=CC=C3)=[CH:22][CH:21]=2)C2C=CC=CC=2)=CC=1.[CH2:53]([N:60]1[CH2:65][CH2:64][N:63]([C:66]2[CH:67]=[C:68](Br)[CH:69]=[C:70]3[C:75]=2[N:74]=[CH:73][CH:72]=[CH:71]3)[CH2:62][CH2:61]1)[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1.C([CH2:84][NH2:85])C1C=CC=CC=1>CCOCC.CC([O-])=O.CC([O-])=O.[Pd+2].C1(C)C=CC=CC=1>[CH2:30]([N:85]([C:68]1[CH:69]=[C:70]2[C:75](=[C:66]([N:63]3[CH2:64][CH2:65][N:60]([CH2:53][C:54]4[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=4)[CH2:61][CH2:62]3)[CH:67]=1)[N:74]=[CH:73][CH:72]=[CH:71]2)[CH3:84])[C:29]1[CH:28]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

8

Edukt 4

HCID 1001PhenethylamineHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 184140798-(4-Benzyl-piperazin-1-yl)-6-bromo-quinoline

Produkt 1

HCID 20701172Benzyl-[8-(4-benzyl-piperazin-1-yl)-quinolin-6-yl]-methyamineAusbeute 407,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 1140TolueneLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To an oven-dried 25 mL round bottom flask was added Cs2CO3 (1.55 g, 4.76 mmol), BINAP (300 mg, 3 mol %), Pd(OAc)2 (100 mg, 3 mol %) and kept under vacuum overnight. To this reaction vessel under a nitrogen atmosphere was added 8-(4-benzyl-piperazin-1-yl)-6-bromo-quinoline (1.3 g, 3.4 mmol), anhydrous toluene (12 mL) and benzylmethylamine (0.53 mL, 4.1 mmol). The reaction mixture was heated at 100° C. overnight. The cooled reaction mixture was diluted with Et2O (15 mL), filtered to remove solids, washed with EtOAc (10 mL) and concentrated. The resulting oil was purified by column chromatography (40% EtOAc/hexane) affording 830 mg (59%) of benzyl-[8-(4-benzyl-piperazin-1-yl)-quinolin-6-yl]-methyamine as an orange foam.

Aufarbeitung

  1. customkept under vacuum overnight
  2. customThe cooled reaction mixture
  3. filtrationfiltered
  4. customto remove solids
  5. washwashed with EtOAc (10 mL)
  6. concentrationconcentrated
  7. customThe resulting oil was purified by column chromatography (40% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-0feb875a3e224eeeb54ad3aa073517b4
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313126B1

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