(S)-2-[2-(1-methyl-2-piperidinyl)ethyl]-benzenamine | 62370-16-5

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: (S)-2-[2-(1-methyl-2-piperidinyl)ethyl]-benzenamine
• 英文别名: 2-[2-[(2S)-1-methylpiperidin-2-yl]ethyl]aniline
• CAS: 62370-16-5
• 化学式: C₁₄H₂₂N₂
• 分子量: 218.342
• InChiKey: CCXFKJBMYLLRBW-ZDUSSCGKSA-N

物化性质

• 沸点：
  342.6±15.0 °C(Predicted)
• 密度：
  1.001±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-[2-(1-methyl-2-piperidinyl)ethyl]-benzenamine 、 3-苯基-2-丙烯酰氯 以 醋酸异丙酯 、 丁酮 为溶剂， 反应 0.33h， 以89.3%的产率得到Iferanserin
  参考文献：
  名称：

  WO2007/111706

  摘要：

  公开号：
• 作为产物：
  描述：

  (S)-[2-(o-aminophenethyl)-1-methylpiperidine dibenzoyl-L-tartrate] 在 碳酸氢钠 作用下， 以 乙酸乙酯 为溶剂， 以100%的产率得到(S)-2-[2-(1-methyl-2-piperidinyl)ethyl]-benzenamine
  参考文献：
  名称：

  Development of a Scalable Synthesis of a Serotonin Receptor Antagonist

  摘要：

  An efficient process was developed for the manufacture of MSA100, a serotonin receptor antagonist, via a five-step synthetic route furnishing a high quality of active pharmaceutical ingredient. Highlights of this synthesis include: (1) replacing carcinogenic methyl iodide with methyl p-toluenesulfonate as the methylating reagent; (2) a hydrogenation protocol with optimized temperature, pressure, and mass-transfer conditions that avoided one side product and reduced the other one effectively; (3) chemical resolution employing D-camphoric acid in a mixed-solvent system; (4) amidation under anhydrous conditions for controlling a Michael adduct impurity; and (5) plausible mechanisms for the formation of side products.

  DOI：

  10.1021/op5003402

文献信息

• Organic Compounds
  申请人：Prashad Mahavir

  公开号：US20090247581A1

  公开（公告）日：2009-10-01

  The present invention relates to a process for the synthesis of (S)-2′[2-1-(methyl-2-piperidyl) ethyl] cinnamanilide (I) or salts or pharmaceutically acceptable prodrugs thereof:

  本发明涉及一种合成(S)-2’[2-1-(甲基-2-哌啶基)乙基]肉桂酰亚胺(I)或其盐或药物可接受的前药的过程。
• S-2'-(2-(1-METHYL-2-PIPERIDYL) ETHYL) CINNAMANILIDE AS A 5-HT2 RECEPTOR ANTAGONIST
  申请人：AMER, M. Samir

  公开号：EP0973741B1

  公开（公告）日：2003-06-11
• ORGANIC COMPOUNDS
  申请人：Novartis AG

  公开号：EP1951670A2

  公开（公告）日：2008-08-06
• [EN] ORGANIC COMPOUNDS<br/>[FR] COMPOSÉS ORGANIQUES
  申请人：NOVARTIS AG

  公开号：WO2007111706A2

  公开（公告）日：2007-10-04

  [EN] The present invention relates to a process for the synthesis of (S)-2'[2-1-(methyl-2-piperidyl) ethyl] cinnamanilide (I) or salts or pharmaceutically acceptable prodrugs thereof.
  [FR] La présente invention concerne un procédé de synthèse de (S)-2'[2-1-(méthyl-2-pipéridyl) éthyl] cinnamanilide (I) ou de sels ou de promédicaments pharmaceutiquement acceptables dudit composé.
• Development of a Scalable Synthesis of a Serotonin Receptor Antagonist
  作者：Mahavir Prashad、Yugang Liu、Wen-Chung Shieh、Frank Schaefer、Bin Hu、Michael Girgis

  DOI：10.1021/op5003402

  日期：2015.1.16

  An efficient process was developed for the manufacture of MSA100, a serotonin receptor antagonist, via a five-step synthetic route furnishing a high quality of active pharmaceutical ingredient. Highlights of this synthesis include: (1) replacing carcinogenic methyl iodide with methyl p-toluenesulfonate as the methylating reagent; (2) a hydrogenation protocol with optimized temperature, pressure, and mass-transfer conditions that avoided one side product and reduced the other one effectively; (3) chemical resolution employing D-camphoric acid in a mixed-solvent system; (4) amidation under anhydrous conditions for controlling a Michael adduct impurity; and (5) plausible mechanisms for the formation of side products.