1-[2-[(4-fluorophenyl)(phenyl)methoxy]ethyl]-4-(3-phenylprypyl)piperazine | 76778-24-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-[2-[(4-fluorophenyl)(phenyl)methoxy]ethyl]-4-(3-phenylprypyl)piperazine
• 英文别名: 1-[2-[(4-fluorophenyl)phenylmethoxy]ethyl]-4-(3-phenylpropyl)piperazine；CV-8282；1-(2-((4-Fluorophenyl)phenylmethoxy)ethyl)-4-(3-phenylpropyl)piperazine；1-[2-[(4-fluorophenyl)-phenylmethoxy]ethyl]-4-(3-phenylpropyl)piperazine
• CAS: 76778-24-0
• 化学式: C₂₈H₃₃FN₂O
• 分子量: 432.581
• InChiKey: NRFRVJIPDSIXRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  15.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[2-[(4-fluorophenyl)(phenyl)methoxy]ethyl]-4-(3-phenylprypyl)piperazine 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以1334 g的产率得到1-[2-[(4-fluorophenyl)phenylmethoxy]ethyl]-4-(3-phenylpropyl)piperazine dihydrochloride
  参考文献：
  名称：

  Scale-Up Synthesis of the Dopamine Uptake Inhibitor GBR-12909

  摘要：

  1-[2-[Bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine (GBR-12909) is a dopamine uptake inhibitor. The development of a robust process for the preparation of this compound in kilogram quantities is described. The primary aims of the development work were to eliminate chromatographic purifications, to minimize the use of environmentally unacceptable reagents, and to improve the overall yield of the three-step convergent process. These objectives were met, with significant improvements obtained in the key coupling reaction of N-(3-phenylpropyl)piperazine dihydrochloride salt with 1-[bis(4-fluorophenyl)methoxy]-2-chloroethane, which was previously low-yielding and lacking in reproducibility.

  DOI：

  10.1021/op020211j
• 作为产物：
  描述：

  苯基丙基哌嗪 在 盐酸 、 sodium carbonate 作用下， 以 乙醇 、 水 、 丁酮 为溶剂， 反应 24.5h， 生成 1-[2-[(4-fluorophenyl)(phenyl)methoxy]ethyl]-4-(3-phenylprypyl)piperazine
  参考文献：
  名称：

  Scale-Up Synthesis of the Dopamine Uptake Inhibitor GBR-12909

  摘要：

  1-[2-[Bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine (GBR-12909) is a dopamine uptake inhibitor. The development of a robust process for the preparation of this compound in kilogram quantities is described. The primary aims of the development work were to eliminate chromatographic purifications, to minimize the use of environmentally unacceptable reagents, and to improve the overall yield of the three-step convergent process. These objectives were met, with significant improvements obtained in the key coupling reaction of N-(3-phenylpropyl)piperazine dihydrochloride salt with 1-[bis(4-fluorophenyl)methoxy]-2-chloroethane, which was previously low-yielding and lacking in reproducibility.

  DOI：

  10.1021/op020211j

文献信息

• ZEE P.; KOGER H. S.; GOOTJES J.; HESPE W., FUR. J. MED. CHEM.-CHIM. THER., 1980, 15, NO 4, 363-370
  作者：ZEE P.、 KOGER H. S.、 GOOTJES J.、 HESPE W.

  DOI：——

  日期：——
• Pharmaceutical compositions for terminating acute episodes of cardiac arrhythmia, restoring sinus rhythm, preventing recurrence of cardiac arrhythmia and/or maintaining normal sinus rhythm in mammals
  申请人：Brown Arthur M.

  公开号：US20120028992A1

  公开（公告）日：2012-02-02

  Disclosed are pharmaceutical compositions for and methods of preventing or treating acute and/or chronic cardiac arrhythmias in a mammal, including terminating acute episodes of cardiac arrhythmia, restoring normal sinus rhythm, preventing recurrence of cardiac arrhythmia and/or maintaining normal sinus rhythm, which contain a combination of 1-[2-[(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine and 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine.
• [EN] PHARMACEUTICAL COMPOSITIONS FOR TERMINATING ACUTE EPISODES OF CARDIAC ARRHYTHMIA, RESTORING SINUS RHYTHM, PREVENTING RECURRENCE OF CARDIAC ARRHYTHMIA, AND/OR MAINTAINING NORMAL SINUS RHYTHM IN MAMMALS<br/>[FR] COMPOSITIONS PHARMACEUTIQUES POUR METTRE FIN À DES ÉPISODES AIGUS D'ARYTHMIE CARDIAQUE, POUR RESTAURER LE RYTHME SINUSAL, POUR PRÉVENIR LA RÉCURRENCE DE L'ARYTHMIE CARDIAQUE ET/OU POUR MAINTENIR UN RYTHME SINUSAL NORMAL CHEZ DES MAMMIFÈRES
  申请人：CHANRX CORP

  公开号：WO2015119938A1

  公开（公告）日：2015-08-13

  A pharmaceutical composition comprising for preventing or treating acute and/or chronic cardiac arrhythmias in an animal comprising an effective amount of 1-[2-[(4-fluorophenyl)(phenyl)methoxy]ethyl]-4-(3-phenylprypyl)piperazine.
• Scale-Up Synthesis of the Dopamine Uptake Inhibitor GBR-12909
  作者：Michael D. Ironside、Priyantha M. Sugathapala、Jerod Robertson、Mark C. P. Darey、Jianzhong Zhang

  DOI：10.1021/op020211j

  日期：2002.9.1

  1-[2-[Bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine (GBR-12909) is a dopamine uptake inhibitor. The development of a robust process for the preparation of this compound in kilogram quantities is described. The primary aims of the development work were to eliminate chromatographic purifications, to minimize the use of environmentally unacceptable reagents, and to improve the overall yield of the three-step convergent process. These objectives were met, with significant improvements obtained in the key coupling reaction of N-(3-phenylpropyl)piperazine dihydrochloride salt with 1-[bis(4-fluorophenyl)methoxy]-2-chloroethane, which was previously low-yielding and lacking in reproducibility.