Reaktion #7274

ord-9059553ff0014d51a2fe1da9bed22a25

Reaktionsgleichung

O=Cc1ccccn1
Pyridine-2-carbaldehyde
CC(NCc1cccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)c1)c1ccccc1
(1H-Benzimidazol-2-ylmethyl)-{3-[(1-phenyl-ethylamino)-methyl]-benzyl}-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine
CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]
sodium triacetoxyborohydride
CC(c1ccccc1)N(Cc1cccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)c1)Cc1ccccn1
title compound
Ausbeute 50.0%
CC(c1ccccc1)N(Cc1cccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)c1)Cc1ccccn1
(1H-Benzimidazol-2-ylmethyl)-(3-{[(1-phenyl-ethyl)-pyridin-2-ylmethyl-amino]-methyl}-benzyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine
Ausbeute 50.0%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigefollowed by purification of the crude material by chromatography on silica gel (2:2:96 CH3OH—NH3 H2O—CH2Cl2)

Vorschrift

Using general procedure B: Reaction of Pyridine-2-carbaldehyde (22 mg, 0.20 mmol, (1H-Benzimidazol-2-ylmethyl)-{3-[(1-phenyl-ethylamino)-methyl]-benzyl}-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (101 mg, 0.20 mmol) and sodium triacetoxyborohydride (58 mg, 0.26 mmol) in CH2Cl2 (2 mL) at room temperature under N2 for 20 h, followed by purification of the crude material by chromatography on silica gel (2:2:96 CH3OH—NH3 H2O—CH2Cl2) afforded the title compound (60 mg, 50%) as a white foam.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07084155B2uspto-grants-2006_08