Reacción #7245

Ecuación de reacción

N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

salicylaldehyde

NaBH(OAc)3

→

amine

Rendimiento 54.0%

N-(2-hydroxyphenylmethyl)-N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

Rendimiento 54.0%

Disolventes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroPurification of the crude material by radial chromatography on silica gel gel (2 mm plate, 75:1:1 CH2Cl2/MeOH/NH4OH)

Procedimiento

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.

Fuente