(4R)-4-(3,4-dichlorophenyl)-N-methyl-3,4-dihydro-2H-naphthalen-1-imine | 312620-95-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (4R)-4-(3,4-dichlorophenyl)-N-methyl-3,4-dihydro-2H-naphthalen-1-imine
• CAS: 312620-95-4
• 化学式: C₁₇H₁₅Cl₂N
• 分子量: 304.219
• InChiKey: MGBVAZJASCWJGJ-GFCCVEGCSA-N

物化性质

• 沸点：
  390.5±42.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4R)-4-(3,4-dichlorophenyl)-N-methyl-3,4-dihydro-2H-naphthalen-1-imine 在 R,S-[Ir(1,5-cyclooctadiene)(PPh₂(C₉H₁₀)(C₃H₃NO-i-Bu))] tetrakis(3,5-bis(trifluoromethyl)phenyl)borate 、 氢气 作用下， 20.0 ℃ 、2.03 MPa 条件下， 反应 12.0h， 生成 (R,R)-舍曲林 、 (1S,4R)-4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine
  参考文献：
  名称：

  Han, Zhaobin; Wang, Zheng; Zhang, Xumu, Angewandte Chemie - International Edition, 2009, vol. 48, p. 5345 - 5349

  摘要：

  DOI：

文献信息

• Highly Steroselective Synthesis of Sertraline
  申请人：Parthasaradhi Reddy Bandi

  公开号：US20070260090A1

  公开（公告）日：2007-11-08

  The present invention relates to a process for highly stereoselective synthesis of sertraline and sertraline intermediate. Thus, the mixture of 4-(3,4-Dichlorophenyl)-3,4-dihydro-N-methyl-1(2H)-naphthalenimine, 5% Pd/CaCO 3 , water and methanol is taken in a hydrogenation flask and then subjected to hydrogenation under a hydrogen pressure of 0.5 Kg at 20-35° C. for 3 hours 30 minutes. The catalyst is removed by filtration and the solvent is evaporated completely under vacuum to obtain cis-(±)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-naphthalen amine. (trans-(±): 0.2).

  本发明涉及一种高立体选择性合成舍曲林和舍曲林中间体的过程。因此，将4-(3,4-二氯苯基)-3,4-二氢-N-甲基-1(2H)-萘亚胺、5% Pd/CaCO3、水和甲醇混合物放入氢化烧瓶中，然后在0.5千克的氢气压力下，在20-35℃下进行3小时30分钟的氢化。通过过滤除去催化剂，然后在真空下完全蒸发溶剂，得到顺式-(±)-4-(3,4-二氯苯基)-1,2,3,4-四氢-N-甲基-萘胺。(反式-(±): 0.2)。
• A HIGHLY STEREOSELECTIVE SYNTHESIS OF SERTRALINE
  申请人：Hetero Drugs Limited

  公开号：EP1885683A2

  公开（公告）日：2008-02-13
• US6506940B1
  申请人：——

  公开号：US6506940B1

  公开（公告）日：2003-01-14
• [EN] A PROCESS FOR CONVERTING STEREOISOMERS OF SERTRALINE INTO SERTRALINE<br/>[FR] PROCEDE PERMETTANT DE CONVERTIR DES STEREOISOMERES DE SERTRALINE EN SERTRALINE
  申请人：SUN PHARMACEUTICAL IND LTD

  公开号：WO2001049638A2

  公开（公告）日：2001-07-12

  A process for converting the cis (1R, 4R), trans (1S, 4R), and trans (1R, 4S) stereoisomers of sertraline into sertraline comprises, providing an initial reaction mixture which contains at least one of these stereoisomers, converting the sertraline stereoisomers into an imine form of sertraline. The imine form of sertraline is then reduced so that sertraline and at least one sertraline stereoisomer byproduct is produced in the reaction mixture. The sertraline is then recovered from the reaction mixture, e.g., by fractional crystallization (followed by resolution of sertraline from the cis (1R, 4R) stereoisomer, if necessary). The reaction mixture is then recycled through the same steps so that sertraline is produced from its stereoisomers in an asymptotic yield.
• [EN] A HIGHLY STEREOSELECTIVE SYNTHESIS OF SERTRALINE<br/>[FR] SYNTHESE HAUTEMENT STEREOSELECTIVE DE SERTRALINE
  申请人：HETERO DRUGS LTD

  公开号：WO2006129324A2

  公开（公告）日：2006-12-07

  [EN] The present invention relates to a process for highly stereoselective synthesis of sertraline and sertraline intermediate. Thus, the mixture of 4-(3,4-Dichlorophenyl)-3,4-dihydro-N-methyl-1(2H)-naphthalenimine, 5 % Pd/CaCO₃, water and methanol is taken in a hydrogenation flask and then subjected to hydrogenation under a hydrogen pressure of 0.5 Kg at 20 - 35°C for 3 hours 30 minutes. The catalyst is removed by filtration and the solvent is evaporated completely under vacuum to obtain cis-(±)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-naphthalen amine. (trans-(±): 0.2).
  [FR] La présente invention concerne un procédé de synthèse hautement stéréosélective de sertraline et d'un produit intermédiaire de sertraline. Un mélange renfermant une 4-(3,4-dichlorophényl)-3,4-dihydro-N-méthyl-1(2H)-naphtalénimine, 5 % de Pd/CaCO₃, de l'eau et du méthanol est introduit dans un flacon d'hydrogénation, puis soumis à une hydrogénation sous une pression d'hydrogène de 0,5 Kg à 20-35 °C pendant 3 heures et 30 minutes. Le catalyseur est enlevé par filtration et le solvant est complètement évaporé sous vide en vue de l'obtention d'une cis-(?)-4-(3,4-dichlorophényl)-1,2,3,4-tétrahydro-N-méthyl-naphtalènamine.