(1-(2-chloroethyl)piperidin-4-yl)(phenyl)methanone | 195507-51-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1-(2-chloroethyl)piperidin-4-yl)(phenyl)methanone
• 英文别名: phenyl-1-(2-chloroethyl)piperidin-4-yl-methanone；1-(2-chloroethyl)-4-benzoylpiperidine；[1-(2-chloroethyl)piperidin-4-yl]-phenylmethanone
• CAS: 195507-51-8
• 化学式: C₁₄H₁₈ClNO
• 分子量: 251.756
• InChiKey: LZFQPFGGUFULHI-UHFFFAOYSA-N

物化性质

• 沸点：
  364.5±37.0 °C(Predicted)
• 密度：
  1.126±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1-(2-chloroethyl)piperidin-4-yl)(phenyl)methanone 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 3.0h， 生成 二苯基(奎宁环-4-基)甲醇
  参考文献：
  名称：

  乌美溴铵的便捷新合成

  摘要：

  摘要 Umeclidinium bromide 是一种用于慢性阻塞性肺疾病的药物，它是通过一种新的苯基（奎宁环-4-基）甲酮中间体合成的。这种新方法操作流程简单，试剂便宜，适合扩大规模。整个四步过程以 29% 的收率和高达 99.83% 的纯度提供了溴化乌美溴铵。首次报道了药物分子的 X 射线晶体结构。图形概要

  DOI：

  10.1080/00397911.2017.1348525
• 作为产物：
  描述：

  4-苯甲酰基哌啶盐酸盐 在 氯化亚砜 、 potassium carbonate 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 32.0h， 生成 (1-(2-chloroethyl)piperidin-4-yl)(phenyl)methanone
  参考文献：
  名称：

  3- [2- [4-(4-Fluorobenzoyl)piperidin- 1-yl]ethyl] -5,6,7,8-tetrahydro-4(3H)-quinazolinones: serotonin 5-HT2A receptor antagonists endowed with potent central action

  摘要：

  A series of 5,6,7,8-tetrahydro-4(3H)-quinazolinones substituted at the 3-position with 4-benzoyl-1-ethylpiperidine, 4-(4-fluorobenzoyl)-1-ethylpiperidine, 4-[bis-(4-fluorophenyl)methylene]-1-ethylpiperidine, or 4-(4-fluorophenyl)-1-propylpiperazine have been prepared and evaluated in binding assays to determine their affinity at serotonin 5-HT2A receptors as well as in a functional test, ie, wet dog shakes (WDS) induced by L-5-hydroxytryptophan (L-5-HTP), a behavioural response which is mediated by stimulation of 5-HT receptors. Among the compounds prepared. 3-[2-[4-(4-fluorobenzoyl)piperidin-1-yl]ethyl]-5,6,7,8-tetrahydro-4(3H)-quinazolinone (10b) and 2-methyl-3-[2-[4-(4-fluorobenzoyl)piperidin-1-yl]ethyl]-5,6,7,8-tetrahydro-4(3H)-quinazolinone (10b) proved to be the most potent 5-HT,, receptor antagonists. In binding assays, the two compounds displayed similar affinity for 5-HT, receptors in the nanomolar range to ketanserin and ritanserin. In the WDS test, they were even more potent than ketanserin and ritanserin. Compound 10b, which was found to possess the highest potency and duration of action in the WDS test, was chosen for a preliminary evaluation of its ability to inhibit ethanol intake in rats, a response linked to blockade of the central 5-HT2A, receptors. This compound significantly reduced ethanol intake in rats from the first day of treatment. The results of the present study indicate that 10b is a potent centrally acting antagonist at 5-HT2A receptors.

  DOI：

  10.1016/s0223-5234(97)83291-6

文献信息

• Substituted cyclic amine compound, production process thereof and
  申请人：Toa Eiyo, Ltd.

  公开号：US05728835A1

  公开（公告）日：1998-03-17

  A substituted cyclic amine compound represented by the following general formula (1) ##STR1## wherein each of R.sup.1 to R.sup.5 represents a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group or the like, A represents a carbonyl group or a sulfonyl group, B represents a methine moiety or a nitrogen atom, D represents a methine moiety, a nitrogen atom or .dbd.N(.fwdarw.O)-- and n is an integer of 2 to 3; and synthetic methods thereof. The inventive compound is useful in preventing and treating circulatory organ-related diseases such as hypertension, ischemic heart disease, cerebrovascular disease, peripheral circulatory disease and the like.

  一种代表如下一般式（1）的替代环胺化合物 ##STR1## 其中R.sup.1到R.sup.5中的每一个代表氢原子、卤素原子、低烷基、低烷氧基或类似物，A代表羰基或磺酰基，B代表亚甲基团或氮原子，D代表亚甲基团、氮原子或.dbd.N(.fwdarw.O)--，n为2至3的整数；以及其合成方法。这种创新化合物在预防和治疗循环系统相关疾病，如高血压、缺血性心脏病、脑血管疾病、周围循环疾病等方面具有用处。
• 1-氮杂双环[2,2,2]辛-4-基苯基酮化合物及 其制备方法和应用
  申请人：扬州奥锐特药业有限公司

  公开号：CN108069956B

  公开（公告）日：2021-03-16

  本发明提供了1‑氮杂双环[2,2,2]辛‑4‑基苯基酮及其制备方法与应用。1‑氮杂双环[2,2,2]辛‑4‑基苯基酮经检测确证其结构为化合物1，该化合物可用于制备治疗慢性阻塞性肺疾病(COPD)的药物芜地溴铵。即通过4‑苯甲酰基哌啶制得1‑(2‑氯乙基)‑4‑苯甲酰基哌啶，再关环得化合物1，进一步与苯基亲核试剂加成，成盐得芜地溴铵。本发明方法成本低，操作简便，适于工业化生产，有较大的应用价值。
• [EN] PROCESS FOR THE PREPARATION OF A NOVEL UMECLIDINIUM SYNTHESIS INTERMEDIATE<br/>[FR] PROCÉDÉ DE PRÉPARATION D'UN NOUVEL INTERMÉDIAIRE DE SYNTHÈSE D'UMECLIDINIUM
  申请人：OLON SPA

  公开号：WO2018220501A1

  公开（公告）日：2018-12-06

  The present invention relates to a process for the preparation of a novel and versatile synthesis intermediate and its use in the preparation of umeclidinium. The invention also relates to some reference standards allowing to detect impurity traces recurring in the preparation of umeclidinium and a process for their preparation.

  本发明涉及一种制备新颖、多用途合成中间体并将其用于制备乌美克替尼的方法。本发明还涉及一些参考标准，可以检测在制备乌美克替尼过程中经常出现的杂质痕迹，并提供一种制备它们的方法。
• Process for the preparation of a novel umeclidinium synthesis intermediate
  申请人：OLON S.P.A.

  公开号：US11028082B2

  公开（公告）日：2021-06-08

  The present invention relates to a process for the preparation of a novel and versatile synthesis intermediate and its use in the preparation of umeclidinium. The invention also relates to some reference standards allowing to detect impurity traces recurring in the preparation of umeclidinium and a process for their preparation.

  本发明涉及一种新型多功能合成中间体的制备工艺及其在乌美拉啶制备中的应用。本发明还涉及一些可检测乌美拉啶制备过程中反复出现的杂质痕量的参考标准及其制备工艺。
• PROCESS FOR THE PREPARATION OF A NOVEL UMECLIDINIUM SYNTHESIS INTERMEDIATE
  申请人：OLON S.p.A.

  公开号：EP3630756A1

  公开（公告）日：2020-04-08