1-(2-氯乙基)-4-[3-(三氟甲基)苯基]哌嗪二盐酸盐 | 57061-71-9

• 物质功能分类: 医药中间体 - 杂环化合物 - 哌嗪类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 中文名称: 1-(2-氯乙基)-4-[3-(三氟甲基)苯基]哌嗪二盐酸盐
• 英文名称: N-(3-trifluoromethylphenyl)-N'-(2-chloroethyl)-piperazine
• 英文别名: 1-chloro-2-[4-(3-trifluoromethylphenyl)piperazin-1-yl]ethane；1-(2-Chloroethyl)-4-[3-(trifluoromethyl)phenyl]piperazine
• CAS: 57061-71-9
• 化学式: C₁₃H₁₆ClF₃N₂
• mdl: MFCD08061400
• 分子量: 292.732
• InChiKey: LEOMYSVONJGULL-UHFFFAOYSA-N

物化性质

• 沸点：
  352.6±42.0 °C(Predicted)
• 密度：
  1.244±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.538
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2-氯乙基)-4-[3-(三氟甲基)苯基]哌嗪二盐酸盐 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以67.3%的产率得到1-(2-azidoethyl)-4-(3-trifluoromethylphenyl)piperazine
  参考文献：
  名称：

  Accelerated Koenigs−Knorr Glucuronidation of a Deactivated Nitrophenol:  Unveiling the Role of Polyamine Additive 1,1,4,7,10,10-Hexamethyltriethylenetetramine¹ through Design of Experiments

  摘要：

  1,1,4,7,10,10-Hexamethyltriethylenetetramine (HMTTA) emerged from a limited parallel screening of selected polyamines as the most appropriate additive for an especially problematic Koenigs-Knorr glucuronidation. This initial finding rapidly evolved into a reliable and high-yielding procedure through the use of two sets of experimental designs. The detailed effect of the stoichiometry of reagents and the amount of amine additive on reaction yield was elucidated. The complexity of the response surface for product yield, described by a third-order polynomial equation, together with ancillary kinetic experiments evidenced the multiple role of HMTTA in the present glucuronidation process.

  DOI：

  10.1021/jo035285n
• 作为产物：
  描述：

  4-[3-(三氟甲基)苯基]-1-哌嗪乙醇 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以96.6%的产率得到1-(2-氯乙基)-4-[3-(三氟甲基)苯基]哌嗪二盐酸盐
  参考文献：
  名称：

  4-(3-三氟甲基苯基)-1-哌嗪-乙醇、氟班色林中间体、氟班色林的合成方法

  摘要：

  本发明公开了一种4‑(3‑三氟甲基苯基)‑1‑哌嗪‑乙醇、氟班色林中间体、氟班色林的合成方法，该4‑(3‑三氟甲基苯基)‑1‑哌嗪‑乙醇的合成方法具体为将间溴三氟甲苯加入第一有机溶剂中，在钯类催化剂、配体和碱的作用下与N‑羟乙基哌嗪反应制得4‑(3‑三氟甲基苯基)‑1‑哌嗪‑乙醇，反应选择性强，收率高，杂质少，为后续氟班色林中间体和氟班色林的合成提供了良好的基础。在此基础上进行氟班色林中间体、氟班色林的合成，反应收率高，合成路线短且杂质少，适合商业化生产。

  公开号：

  CN114085197A

文献信息

• Novel aminoalkylthio derivatives of triazolopyridine or
  申请人：Centre D'Activite Et De Recherches Pharmaceutique Industrielle

  公开号：US04886805A1

  公开（公告）日：1989-12-12

  The present invention relates to novel compounds corresponding to the formula: ##STR1## in which: n represents an integer between 1 and 8 and optimally 2 or 3; (CH.sub.2).sub.n --N can also form a ring or a heterocycle, for example having 5 to 7 atoms and preferably 6 atoms; R.sub.1 and R.sub.2 can represent hydrogen or a lower alkyl having 1 to 5 carbon atoms or can form, together with the nitrogen, a ring such as pyrrolidine, piperidine, morpholine, thiomorpholine, phenyltetrahydropyridine, piperazine or piperazine N-substituted by an alkyl, a phenyl or a heterocycle; in the case of the phenyltetrahydropyridines and the phenylpiperazines or heteroarylpiperazines, the phenyl or the heterocycle may or may not be substituted by halogens or methoxy, thiomethyl, hydroxyl, nitro, amino, cyano, lower alkyl, trifluoromethyl or trichloromethyl groups; and R.sub.3, R.sub.4 and R.sub.5 can represent hydrogen, a lower alkyl, a hydroxyalkyl or hydroxybenzyl group, a halogen, a trifluoromethyl, a methoxy, a thiomethyl or a nitro or two of them can form a ring, in particular a phenyl in the case of the triazoloquinolines or the triazoloisoquinolines; and the non-toxic acid addition salts. These products are useful as drugs and possess analgesic properties, acting especially on the central nervous system as minor tranquilizers.

  本发明涉及通式为##STR1##的新颖化合物，其中：n代表1至8之间的整数，最优选2或3；(CH.sub.2).sub.n --N也可以形成环或杂环，例如具有5至7个原子，优选6个原子；R.sub.1和R.sub.2可以代表氢或具有1至5个碳原子的低级烷基，或者可以与氮一起形成环，如吡咯烷、哌啶、吗啉、硫代吗啉、苯并四氢吡啶、哌嗪或由烷基、苯基或杂环取代的哌嗪N；在苯并四氢吡啶和苯基哌嗪或杂环哌嗪的情况下，苯基或杂环可以被卤素、甲氧基、硫甲基、羟基、硝基、氨基、氰基、低级烷基、三氟甲基或三氯甲基取代或不取代；R.sub.3、R.sub.4和R.sub.5可以代表氢、低级烷基、羟基烷基或羟基苄基、卤素、三氟甲基、甲氧基、硫甲基或硝基，其中两个可以形成环，特别是在三唑并喹啉或三唑并异喹啉的情况下形成苯环；以及无毒的酸加成盐。这些产品作为药物有用，并具有镇痛特性，特别作用于中枢神经系统作为轻度镇静剂。
• 苯骈氮杂烷基芳基哌嗪衍生物及在制备药物中的应用
  申请人：江苏恩华药业股份有限公司

  公开号：CN109280030B

  公开（公告）日：2022-04-22

  本发明公开了一种苯骈氮杂烷基芳基哌嗪衍生物及在制备药物中的应用，所述的苯骈氮杂烷基芳基哌嗪衍生物显示出对中枢神经系统的作用，特别是对5‑HT1A受体和Sigma‑1受体的双重高亲和活性作用，体内发挥多种生理和药理作用，可用作药物活性物质，特别是用于抗抑郁、抗焦虑、抗双向情感障碍、抗神经性疼痛，并且还可以用作制备其它药物活性化合物的中间体。本发明的化合物药效显著、毒副作用小，能够满足临床应用的需要，为具有如下结构式(IV)的化合物或其游离碱或盐：
• Synthesis of Mannich Bases of Arylidenepyridazinones as Analgesic Agents
  作者：Catherine Rubat、Pascal Coudert、Eliane Albuisson、Janine Bastide、Joele Couquelet、Pierre Tronche

  DOI：10.1002/jps.2600811108

  日期：1992.11

  A series of 5-arylidenepyridazin-3-ones substituted in the 2-position by an arylpiperazinoalkyl moiety (2-16) was synthesized and evaluated for analgesic activity. In the phenylbenzoquinone-induced writhing test, Mannich bases 2-14 were the most active compounds (6.1 < or = ED50 < or = 43.0 mg/kg, orally; ED50 is the half-maximal effective dose). Pyridazinones 8 and 9, with a 3-chlorophenylpiperazinomethyl

  合成了在2-位被芳基哌嗪子烷基部分（2-16）取代的一系列5-芳基吡啶并嗪-3-酮，并评价了其镇痛活性。在苯基苯醌诱导的扭体试验中，曼尼希碱2-14是活性最高的化合物（口服6.1 <或= ED50 <或= 43.0 mg / kg； ED50是最大有效剂量的一半）。具有3-氯苯基哌嗪子甲基取代基的吡嗪酮8和9也表现出显着的抗炎和退热作用。对苯基苯醌诱导的扭体试验中的活性进行汉斯分析，并获得与亲脂性和哈米特常数的显着相关性。
• Oxazolopyridine compounds
  申请人：Science et Organisation

  公开号：US05084456A1

  公开（公告）日：1992-01-28

  Compounds of general formula (I): ##STR1## in which: R.sub.1 and R.sub.2 each represent a hydrogen atom or, with the oxygen and nitrogen, form an --O--CO--N-- linkage, W represents a halogen atom or a lower alkyl or alkoxy group optionally substituted with one or more halogen atoms, such as trifluoromethyl, and m being between 0 and 3, A represents a linear or branched lower alkylene group, and Ar represents an aryl or heteroaryl group optionally substituted with one or more halogen atoms or with one or more lower alkyl, hydroxy, hydroxysulfonyloxy, lower alkoxy or aryloxy groups optionally substituted with one or more halogen atoms, such as a trifluoromethyl group, on the understanding that lower alkyl or lower alkyloxy radical is understood to mean a linear or branched alkyl group comprising from 1 to 6 carbon atom, their isomers, epimers and diastereoisomers. Medicinal products useful in the treatment of pain.

  通式（I）的化合物：##STR1##其中：R.sub.1和R.sub.2分别表示氢原子或与氧和氮形成--O--CO--N--键合，W表示卤原子或一个或多个卤原子，如三氟甲基，可被取代的较低烷基或烷氧基团，m为0到3之间，A表示线性或支链较低烷基团，Ar表示芳基或杂环芳基团，可选地取代一个或多个卤原子或一个或多个较低烷基、羟基、羟基磺酰氧基、较低烷氧基或芳氧基团，可选地取代一个或多个卤原子，如三氟甲基团，其中较低烷基或较低烷氧基基团被理解为包含1到6个碳原子的线性或支链烷基团，它们的异构体、对映异构体和二对映异构体。用于治疗疼痛的药用产品。
• Novel nonopioid non-antiinflammatory analgesics: 3-(aminoalkyl)- and 3-[(4-aryl-1-piperazinyl)alkyl]oxazolo[4,5-b]pyridin-2(3H)-ones
  作者：Christine Flouzat、Yvette Bresson、Anny Mattio、Jacqueline Bonnet、Gerald Guillaumet

  DOI：10.1021/jm00056a010

  日期：1993.2

  A series of 3-(aminoalkyl)- and 3-[(4-aryl-1-piperazinyl)alkyl]oxazolo[4,5-b]pyridin-2(3H)-ones were prepared from their respective oxazolo[4,5-b]pyridin-2(3H)-ones. Several members of this group were found to possess potent analgesic activity in the mouse during a p-phenylquinone writhing induced test. Among them, phenylpiperazine compounds with two-carbon length alkyl chains, 2a and 2b, appeared

  由它们各自的恶唑并[4,5]制备了一系列的3-（氨基烷基）-和3-[（4-芳基-1-哌嗪基）烷基]恶唑并[4,5-b]吡啶-2（3H）-。 -b] pyridin-2（3H）-ones。在对苯醌扭体诱导试验中，发现该组的几名成员在小鼠中具有有效的镇痛活性。其中，具有两碳长度烷基链的苯基哌嗪化合物2a和2b以高止痛剂出现，几乎没有毒性，既不具有抗炎作用也不具有阿片样物质受体亲和力。详细介绍了该系列的合成和结构亲和关系。