Phenethylamine → benzyl-methyl-(2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-6-yl)-amine

HRID 574162Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 574162
Cl[C:2]1[C:10]2[NH:9][C:8]3[CH2:11][CH2:12][N:13]([CH3:15])[CH2:14][C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[Na+].C(P[C:27]1[CH:32]=[C:31](PC(C)(C)C)[CH:30]=[CH:29][C:28]=1[C:38]1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C.C([CH2:60][NH2:61])C1C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[CH2:38]([N:61]([CH3:60])[C:2]1[C:10]2[NH:9][C:8]3[CH2:11][CH2:12][N:13]([CH3:15])[CH2:14][C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:27]=1

Komponenten

7

Edukt 4

HCID 1001PhenethylamineHCID 50915806-Chloro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoleHCID 23676156Sodium t-butoxideHCID 866928022,4Di-tert-butylphosphino-2',4',6'-triisopropyl biphenyl

Produkt 1

HCID 53372368benzyl-methyl-(2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-6-yl)-amineAusbeute 109,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a degassed mixture of 6-chloro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (100 mg, 0.5 mmol), sodium tert-butoxide (576 mg, 6.0 mmol), palladium acetate (22.4 mg, 0.1 mmol) and 2,4 di-tert-butylphosphino-2′,4′,6′-triisopropyl biphenyl (63.0 mg, 0.15 mmol) was added dry toluene (2 mL). After stirring for 5 min, benzylmethylamine (0.09 mL, 0.7 mmol) was added to the reaction mixture, which was stirred at 100° C. for 16 h. The reaction mixture was filtered and residue washed with EtOAc. The filtrate was concentrated under reduced pressure to afford crude material, which was purified by reverse phase HPLC to yield benzyl-methyl-(2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-6-yl)-amine (50 mg). 1H NMR (Freebase, CDCl3) δ (ppm): 7.80 (bs, 1H), 7.38 (m, 4H), 7.28 (m, 1H), 7.10 (s, 1H), 7.0 (t, 1H), 6.78 (d, 1H), 4.28 (s, 2H), 3.70 (s, 2H), 2.86 (m, 4H), 2.78 (s, 3H), 2.58 (s, 3H).

Aufarbeitung

  1. stirringwas stirred at 100° C. for 16 h
  2. filtrationThe reaction mixture was filtered
  3. washresidue washed with EtOAc
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customto afford crude material, which
  6. customwas purified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-ef9552872a884a169e122c73aec12222
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09034865B2

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