4-N-benzyl-1-N-(6-chloropyridin-3-yl)piperazine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 4-N-benzyl-1-N-(6-chloropyridin-3-yl)piperazine
• 英文别名: 1-Benzyl-4-(6-chloropyridin-3-yl)piperazine；1-benzyl-4-(6-chloropyridin-3-yl)piperazine
• 化学式: C₁₆H₁₈ClN₃
• 分子量: 287.792
• InChiKey: ITWQDIYKXZAVGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  19.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-溴-2-氯吡啶 、 1-苄基哌嗪 在 tris(dibenzylideneacetone)dipalladium (0) 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以97%的产率得到4-N-benzyl-1-N-(6-chloropyridin-3-yl)piperazine
  参考文献：
  名称：

  Selective Amination of Polyhalopyridines Catalyzed by a Palladium−Xantphos Complex

  摘要：

  Amination of 5-bromo-2-chloropyridine (1a) catalyzed by a palladium-Xantphos complex predominately gives 5-amino-2-chloropyridine product 3a in 96% isolated yield and excellent chemoselectivity (3a/4a = 97:3). Amination of 2,5-dibromopyridine (11) under the same conditions exclusively affords 2-amino-5-bromopyridine 4a.

  DOI：

  10.1021/ol0357696

文献信息

• A short and efficient synthesis of N-aryl- and N-heteroaryl-N′-(arylalkyl)piperazines
  作者：Dirk Michalik、Kamal Kumar、Alexander Zapf、Annegret Tillack、Michael Arlt、Timo Heinrich、Matthias Beller

  DOI：10.1016/j.tetlet.2004.01.066

  日期：2004.3

  A new synthesis of N-aryl- and N-heteroaryl-N'-(arylalkl)pipeazines using palladium-catalyzed amination of aryl bromicies and heteroaryl chlorides with mono N-benzyl- or N-(arylethyl)piperazines is reported. Most coupling processes proceed in high yield and good selectivity using either diadmantyl-n-butylphosphine (1), 2-(dicyclohexylphosphino)-2'-(N,N-dimethylamino)biphenyl (2), or 2-((di-tert-butylphosphino)biphenyl (3) as ligand. Applying an automated parallel synthesizer the preparation of a small library of potentially bioactive compounds is easily achieved. (C) 2004 Published by Elsevier Ltd.
• Selective Amination of Polyhalopyridines Catalyzed by a Palladium−Xantphos Complex
  作者：Jianguo Ji、Tao Li、William H. Bunnelle

  DOI：10.1021/ol0357696

  日期：2003.11.1

  Amination of 5-bromo-2-chloropyridine (1a) catalyzed by a palladium-Xantphos complex predominately gives 5-amino-2-chloropyridine product 3a in 96% isolated yield and excellent chemoselectivity (3a/4a = 97:3). Amination of 2,5-dibromopyridine (11) under the same conditions exclusively affords 2-amino-5-bromopyridine 4a.