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

Participants

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

Reaction Steps

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.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07084155B2
Source dataset	uspto-grants-2006_08
ORD ID	ord-f5d0730dc5f14fbd876c5c487555fef6
Source note	uspto-grants-2006_08