反应 #7266

ord-9f56ce14538b4073988d127770bef125

反应方程式

COc1ccccc1C(C)=O
1-(2-methoxy-phenyl)-ethanone
NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1
N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine
CC(=O)O
AcOH
CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]
NaBH(OAc)3
COc1ccccc1C(C)NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1
desired product
收率 31.2%
COc1ccccc1C(C)NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1
(1H-benzimidazol-2-ylmethyl)-(4-{[1-(2-methoxy-phenyl)-ethylamino]-methyl}-benzyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine
收率 31.2%

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 light yellow foam (267 mg) by column chromatography on silica gel (100:1:1—CH2Cl2:MeOH:NH4OH)

实验过程

Using General Procedure B: To a stirred solution of 1-(2-methoxy-phenyl)-ethanone (69 uL, 0.50 mmol), N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (200 mg, 0.50 mmol) and AcOH (0.10 mL, 1.4 mmol) in THF (5 mL) was added NaBH(OAc)3 and the mixture was stirred at room temperature for 48 hours. Purification of the crude light yellow foam (267 mg) by column chromatography on silica gel (100:1:1—CH2Cl2:MeOH:NH4OH) followed by radial chromatography on silica gel (100:1:1—CH2Cl2:MeOH:NH4OH) afforded the desired product (83 mg, 27%) as a white foam.

来源

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