N-(3-phenylpropyl)piperazine dihydrochloride salt

• 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: N-(3-phenylpropyl)piperazine dihydrochloride salt
• 英文别名: 1-(3-phenylpropyl)-piperazine dihydrochloride；4-(3-phenylpropyl)piperazine dihydrochloride；1-(3-Phenylpropyl)piperazin-4-ium;chloride
• 化学式: C₁₃H₂₀N₂*2ClH
• 分子量: 277.237
• InChiKey: CSEXKCDPFLQHQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.95
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  15.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(3-phenylpropyl)piperazine dihydrochloride salt 、 2-[bis(4-fluorophenyl)methoxy]ethyl iodide 在 sodium carbonate 作用下， 以 水 、 丁酮 为溶剂， 反应 24.0h， 生成 伐诺司林
  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 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以111.5 g的产率得到N-(3-phenylpropyl)piperazine dihydrochloride salt
  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

• ω-Quinazolinonylalkyl aryl ureas as reversible inhibitors of monoacylglycerol lipase
  作者：Florian M. Dato、Jörg-Martin Neudörfl、Michael Gütschow、Bernd Goldfuss、Markus Pietsch

  DOI：10.1016/j.bioorg.2019.103352

  日期：2020.1

  The serine hydrolase monoacylglycerol lipase (MAGL) is involved in a plethora of pathological conditions, in particular pain and inflammation, various types of cancer, metabolic, neurological and cardiovascular disorders, and is therefore a promising target for drug development. Although a large number of irreversible-acting MAGL inhibitors have been discovered over the past years, there are only few

  丝氨酸水解酶单酰基甘油脂肪酶（MAGL）涉及多种病理状况，特别是疼痛和炎症，各种类型的癌症，代谢，神经和心血管疾病，因此是药物开发的有希望的靶标。尽管在过去几年中发现了许多不可逆作用的MAGL抑制剂，但到目前为止，只有很少的已知化合物可逆地抑制酶。因此，在显示出可逆的抑制行为的新型化学实体上投入了大量的精力，认为这种化学实体引起较少的不良副作用。为了探索各种化学结构作为MAGL粘合剂，我们已经应用了一种虚拟筛选方法，即将小分子停靠在人类MAGL（hMAGL）的晶体结构中，并设想了45种选定化合物的库，然后将其合成。生化研究包括确定对hMAGL和两种相关水解酶的抑制能力，即人脂肪酸酰胺水解酶（hFAAH）和鼠类胆固醇酯酶（mCEase）。这些分析中最有希望的候选物，即三个带有3至5个亚甲基的烷基间隔基的ω-喹唑啉酮烷基烷基芳基脲，IC50值为20-41 µM，对hMAGL具有可逆的去污剂不敏
• 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.