4-(((6-cyclopropyl-4-(trifluoromethyl)pyridine-2-yl)methoxy)methyl)-4-(4-fluorophenyl)-1-methylpiperidin-1-ium chloride | 1421961-56-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-(((6-cyclopropyl-4-(trifluoromethyl)pyridine-2-yl)methoxy)methyl)-4-(4-fluorophenyl)-1-methylpiperidin-1-ium chloride
• 英文别名: 2-Cyclopropyl-6-[[4-(4-fluorophenyl)-1-methylpiperidin-4-yl]methoxymethyl]-4-(trifluoromethyl)pyridine;hydrochloride；2-cyclopropyl-6-[[4-(4-fluorophenyl)-1-methylpiperidin-4-yl]methoxymethyl]-4-(trifluoromethyl)pyridine;hydrochloride
• CAS: 1421961-56-9
• 化学式: C₂₃H₂₆F₄N₂O*ClH
• 分子量: 458.927
• InChiKey: KHPLWRGEKWAUDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.72
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  25.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N-Boc-4-哌啶甲酸乙酯 在 盐酸 、 lithium aluminium tetrahydride 、 正丁基锂 、 dimethyl sulfide borane 、 potassium-tert-amylate 、 水 、 二环己胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 2-甲基四氢呋喃 、 乙醇 、 二氯甲烷 、 异丙醇 、 甲苯 为溶剂， 反应 27.55h， 生成 4-(((6-cyclopropyl-4-(trifluoromethyl)pyridine-2-yl)methoxy)methyl)-4-(4-fluorophenyl)-1-methylpiperidin-1-ium chloride
  参考文献：
  名称：

  Development of a Scalable Route to a Dual NK-1/Serotonin Receptor Antagonist

  摘要：

  The evolution of a process for the preparation of a new heterocyclic dual NK1/serotonin receptor antagonist is described. The final synthesis features a telescoped sequence in which an iron(III)-catalyzed Grignard coupling is followed by a benzylic chlorination utilizing trichlorocyanuric acid to construct an unsymmetrical 2,4,6-trisubstituted pyridine. Etherification of a 4,4'-arylhydroxymethane substituted piperidine fragment completes the synthesis of the active pharmaceutical ingredient in 44% overall yield.

  DOI：

  10.1021/op300323k

文献信息

• Development of a Scalable Route to a Dual NK-1/Serotonin Receptor Antagonist
  作者：Christina Risatti、Kenneth J. Natalie、Zhongping Shi、David A. Conlon

  DOI：10.1021/op300323k

  日期：2013.2.15

  The evolution of a process for the preparation of a new heterocyclic dual NK1/serotonin receptor antagonist is described. The final synthesis features a telescoped sequence in which an iron(III)-catalyzed Grignard coupling is followed by a benzylic chlorination utilizing trichlorocyanuric acid to construct an unsymmetrical 2,4,6-trisubstituted pyridine. Etherification of a 4,4'-arylhydroxymethane substituted piperidine fragment completes the synthesis of the active pharmaceutical ingredient in 44% overall yield.