反应 #7245

ord-f5d0730dc5f14fbd876c5c487555fef6

反应方程式

NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1
N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine
O=Cc1ccccc1O
salicylaldehyde
CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]
NaBH(OAc)3
Oc1ccccc1CNCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1
amine
收率 54.0%
Oc1ccccc1CNCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1
N-(2-hydroxyphenylmethyl)-N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine
收率 54.0%

溶剂

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

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

实验过程

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.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US07084155B2uspto-grants-2006_08