Salicylaldehyde → n-(2-Hydroxyphenylmethyl)-n'-(1h-benzimidazol-2-ylmethyl)-n'-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	Salicylaldehyde	HCID 6998	—
Edukt	Sodium triacetoxyborohydride	HCID 5049666	—
Edukt	N-[(1H-Benzo[d]imidazol-2-yl)methyl]-N-(4-(aminomethyl)-benzyl)-5,6,7,8-tetrahydroquinolin-8-amine	HCID 21985008	—
Lösungsmittel	Dichloromethane	HCID 6344	—
Produkt	n-(2-Hydroxyphenylmethyl)-n'-(1h-benzimidazol-2-ylmethyl)-n'-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine	HCID 22018567	54%

Reaktionsschritte

Using General Procedure B: To a stirred solution of N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (147 mg, 0.37 mmol) and salicylaldehyde (0.04 mL, 0.38 mmol) in CH2Cl2 (5 mL) was added NaBH(OAc)3 (100 mg, 0.47 mmol) and the resultant mixture was stirred at room temperature for 16 hours. Purification of the crude material by radial chromatography on silica gel gel (2 mm plate, 75:1:1 CH2Cl2/MeOH/NH4OH) afforded the free amine (100 mg, 54%) as a white foam.

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US07084155B2
Quelldatensatz	uspto-grants-2006_08
ORD ID	ord-f5d0730dc5f14fbd876c5c487555fef6
Quellennotiz	uspto-grants-2006_08