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

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	2-Chlorobenzoxazole	HCID 11986	—
Reactant	N-[(1H-Benzo[d]imidazol-2-yl)methyl]-N-(4-(aminomethyl)-benzyl)-5,6,7,8-tetrahydroquinolin-8-amine	HCID 21985008	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	n-(Benzoxazol-2-yl)-n'-(1h-benzimidazol-2-ylmethyl)-n'-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine	HCID 22018820	50.4%

Reaction Steps

Using the General N-Alkylation Procedure: To a stirred solution of N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (128 mg, 0.32 mmol) and triethylamine (100 ul, 0.72 mmol) in THF (5 mL) was added 2-chlorobenzoxazole (50 uL, 0.44 mmol) and the mixture was stirred at reflux for 16 h. Purification of the crude material by radial chromatography on silica gel (1 mm plate, CH2Cl2/MeOH/NH4OH, 125:1:1) afforded the desired amine (83 mg, 37%) as a yellow foam.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07084155B2
Source dataset	uspto-grants-2006_08
ORD ID	ord-ac86493adafa4fabbddb1c0ee2a32e96
Source note	uspto-grants-2006_08