(alphaR)-alpha-甲基-N-[3-(3-甲基苯基)丙基]-1-萘甲胺 | 253337-60-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: (alphaR)-alpha-甲基-N-[3-(3-甲基苯基)丙基]-1-萘甲胺
• 中文别名: 西那卡塞杂质9
• 英文名称: 3-(3-methylphenyl)-N-[(1R)-1-(1-naphthyl)ethyl]propan-1-amine
• 英文别名: 3-(3-methyphenyl)-N-[(1R)-1-(1-naphthyl)ethyl]propan-1-amine；(R)-N-(1-(naphthalen-1-yl)ethyl)-3-(m-tolyl)propan-1-amine；3-(3-methylphenyl)-N-[(1R)-1-naphthalen-1-ylethyl]propan-1-amine
• CAS: 253337-60-9
• 化学式: C₂₂H₂₅N
• 分子量: 303.447
• InChiKey: BREGDWXNNPCUFR-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (R)-1-(1-萘基)乙胺 、 1-(3-溴丙基)-3-甲基苯 在 苯甲醛 、 盐酸 、 水 作用下， 以 N-甲基吡咯烷酮 、 甲苯 为溶剂， 以55.92%的产率得到(alphaR)-alpha-甲基-N-[3-(3-甲基苯基)丙基]-1-萘甲胺
  参考文献：
  名称：

  Method For The Preparation Of Cinacalcet And Intermediates And Impurities Thereof

  摘要：

  揭示了一种制备Cinacalcet的方法，包括处理(R)-1-萘乙胺和芳香醛以形成公式(IV)的(1R)-1-(2-萘基)-N-(芳基亚甲基)乙胺衍生物，进一步用公式(V)的1-(3-卤代丙基)-3-(三氟甲基)苯与其反应以获得公式(VI)的亚胺盐，随后水解以获得Cinacalcet的自由基。

  公开号：

  US20110319663A1

文献信息

• PROCESSES FOR THE PREPARATION OF CINACALCET
  申请人：Mukhtar Sayeed

  公开号：US20120309842A1

  公开（公告）日：2012-12-06

  The present invention provides processes and intermediates for preparing cinacalcet base and pharmaceutically acceptable salts thereof.

  本发明提供了制备西那卡塞碱及其药用可接受盐的过程和中间体。
• [EN] PROCESS FOR PREPARING CINACALCET<br/>[FR] PROCEDE DE PREPARATION DE CINACALCET
  申请人：ZACH SYSTEM SPA

  公开号：WO2011029833A1

  公开（公告）日：2011-03-17

  A process for preparing N-[(1R)-1-(1-naphthyl)ethyl]-3-[3-(trifluoromethyl)-phenyl]propan-1-amine of formula hydrochloride salt of formula (I); i.e. Cinacalcet.HC1 and its intermediate of formula (IX).

  一种制备化学式为盐酸盐(I)的N-[(1R)-1-(1-萘基)乙基]-3-[3-(三氟甲基)苯基]丙基胺（即Cinacalcet.HCl）及其中间体化学式为(IX)的方法。
• PROCESSES FOR PREPARING INTERMEDIATE COMPOUNDS USEFUL FOR THE PREPARATION OF CINACALCET
  申请人：Szekeres Tibor

  公开号：US20100267988A1

  公开（公告）日：2010-10-21

  The invention relates, in general, to an improved process for preparing compounds (e.g., 3-(3-trifluoromethylphenyl)propanal (Compound III, below)), which are key intermediates for the synthesis of cinacalcet, its salts and/or solvates thereof, as well as the use of such compounds prepared by such process for the preparation of cinacalcet and/or its salts or solvates.

  该发明涉及一种改进的制备化合物的方法（例如，3-（3-三氟甲基苯基）丙醛（下图中的化合物III）），这些化合物是合成西那卡塞特及其盐和/或溶剂的关键中间体，以及通过该方法制备的这些化合物用于制备西那卡塞特和/或其盐或溶剂的用途。
• Method for the preparation of cinacalcet and intermediates and impurities thereof
  申请人：Mathad Vijayavitthal Thippannachar

  公开号：US08575395B2

  公开（公告）日：2013-11-05

  A method for the preparation of Cinacalcet is disclosed comprising treating (R)-1-naphthyl ethylamine with an aromatic aldehyde to form (1R)-1-(2-naphthyl)-N-(aryl methylene)ethanamine derivative of Formula (IV), which is further treated with 1-(3-halopropyl)-3-(trifluoromethyl)benzene of Formula (V) to obtain an iminium salt of Formula (VI), followed by hydrolysis to obtain Cinacalcet free base.

  本发明揭示了一种制备西那卡塞的方法，包括将(R)-1-萘乙胺与芳香醛处理以形成公式(IV)的(1R)-1-(2-萘基)-N-(芳基亚甲基)乙胺衍生物，进一步用公式(V)的1-(3-卤代丙基)-3-(三氟甲基)苯与其反应，得到公式(VI)的亚胺盐，随后水解得到西那卡塞游离碱。
• Industrial Application of the Forster Reaction: Novel One-Pot Synthesis of Cinacalcet Hydrochloride, a Calcimimetic Agent
  作者：Gorakshanath B. Shinde、Navnath C. Niphade、Shrikant P. Deshmukh、Raghunath B. Toche、Vijayavitthal T. Mathad

  DOI：10.1021/op200016a

  日期：2011.3.18

  Described is a new, practical, and one-pot process, based on the Forster reaction, for the synthesis of cinacalcet hydrochloride (1), a calcimimetic agent and calcium-sensing receptor antagonist. The synthesis comprises the condensation of (1R)-(+)-1-naphthylethyl amine (2) with benzaldehyde (3) followed by reaction of obtained Schiff's base 4 with 1-(3-halopropyl)-3-(trifluoromethyl)-benzene (5) to provide highly unstable iminium salt 6. Subsequent hydrolysis of 6 with water in the same pot yielded cinacalcet. The treatment of cinacalcet with hydrochloric acid during the workup process furnished 1 with an overall yield of around 60%. Our synthetic approach for 1, discussed in this report demonstrates industrial application of the century-old, unexplored name reaction, "Forster's Reaction" or Forster-Decker synthesis.