2-(2-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)ethoxy)acetamide | 163837-43-2

• 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: 2-(2-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)ethoxy)acetamide
• 英文别名: 2-[2-[4-[(4-chlorophenyl)-phenylmethyl]piperazin-1-yl]ethoxy]acetamide
• CAS: 163837-43-2
• 化学式: C₂₁H₂₆ClN₃O₂
• 分子量: 387.909
• InChiKey: LVJDQBJDVOYDLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  58.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)ethoxy)acetamide 在 盐酸 作用下， 以71%的产率得到cetirizine dihydrochloride
  参考文献：
  名称：

  A Novel Synthesis of the Enantiomers of an Antihistamine Drug by Piperazine Formation from a Primary Amine

  摘要：

  报道了抗组胺药物2(2-{4-[(4-氯苯基)苯基甲基]-1-哌嗪基}乙氧基)乙酸二盐酸盐(1)的每个对映异构体的对映选择性合成方法，涉及从4-氯苯甲胺的每个对映异构体与N,N-双(2-氯乙基)-4-甲基苯磺酰胺反应制备分子中的苯甲酰基哌嗪部分。介绍了对标准的甲苯磺酰胺去保护方法的改进，用氢溴酸在醋酸中进行去保护，并用4-羟基苯甲酸替代苯酚。

  DOI：

  10.1055/s-1995-4013
• 作为产物：
  描述：

  cetirizine dihydrochloride 在 氨 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 2-(2-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)ethoxy)acetamide
  参考文献：
  名称：

  A Large-Scale Synthesis of Enantiomerically Pure Cetirizine Dihydrochloride Using Preparative Chiral HPLC

  摘要：

  Enantiomerically pure cetirizine can be prepared by preparative HPLC separation of cetirizine amide, The amide has an alpha value of 2.76 (USP resolution of 8.54) using a Chiralpak AD column, and 0.5 wt % of the amide (based on packing material) can be injected per run.

  DOI：

  10.1021/op0002951

文献信息

• Process for preparing (S) and (R)—2-[4-(4-chlorobenzhydryl)piperazin-1-yl]-ethoxyacetamide
  申请人：Zimmerman Vincent

  公开号：US06977301B1

  公开（公告）日：2005-12-20

  The present invention relates to a process for preparing (S)-2-[4-(4-chlorobenzhydryl)piperazin-1-yl]-ethoxyacetamide and (R)-2-[4-(4-chlorobenzhydryl)piperazin-1-yl]-ethoxyacetamide by separation of a racemic mixture using multiple column chromatography.

  本发明涉及一种通过使用多柱色谱分离外消旋混合物来制备(S)-2-[4-(4-氯苯基)-1-哌嗪基]-乙氧基乙酰胺和(R)-2-[4-(4-氯苯基)-1-哌嗪基]-乙氧基乙酰胺的方法。
• Process for the preparation of {2-[4-(alpha-phenyl-p-chlorobenzyl)piperazin-1-yl]ethoxy} acetic acid and novel intermediates therefor
  申请人：——

  公开号：US20030092911A1

  公开（公告）日：2003-05-15

  The invention refers to a novel process for the preparation of cetirizine of formula (I) as well as to novel {2-[4-(&agr;-phenyl-p-chloro-benzyl)piperazin-1-yl]ethoxy}acetamides of formula II, wherein R 1 and R 2 represent, independently, a C 1-4 alkyl group optionally substituted by a phenyl group, a C 2-4 alkenyl group or a cyclohexyl group, or R 1 and R 2 form together with the adjacent nitrogen atom a morpholino group. According to the novel process, an acetamide of formula (II) is hydrolized, if desired in the presence of a phase transfer catalyst, to obtain cetirizine.

  该发明涉及一种新型制备化学式（I）的右美沙芬的方法，以及一种新型化学式II的{2-[4-(&agr;-苯基-p-氯苄基)哌嗪-1-基]乙氧}乙酰胺，其中R1和R2分别独立表示C1-4烷基，可选择地被苯基取代，C2-4烯基或环己基，或者R1和R2与相邻的氮原子一起形成吗啡基团。根据这种新型方法，化学式（II）的乙酰胺在需要时在相转移催化剂的存在下水解，以获得右美沙芬。
• Processes for the Synthesis of Levocetirizine and Intermediates for Use Therein
  申请人：Rao Dharmaraj Ramachandra

  公开号：US20110184174A1

  公开（公告）日：2011-07-28

  The present invention provides a compound of formula (IV) wherein R is Cl, Br, NO 2 , OH or OR′, and R′ is alkyl, and its use in the synthesis of levocetirizine, including its use in the synthesis of (−)-1-[(4-chlorophenyl)-phenylmethyl]piperazine, an intermediate useful in the synthesis of levocetirizine. The present invention also provides compounds (II) and (III) which are useful in the synthesis of compound (IV).

  本发明提供了一种化合物，其化学式为(IV)，其中R为Cl、Br、NO2、OH或OR′，R′为烷基，并且其在左旋西替利嗪的合成中的应用，包括其在合成(−)-1-[(4-氯苯基)-苯甲基]哌嗪中的应用，这是左旋西替利嗪合成中有用的中间体。本发明还提供了化合物(II)和(III)，它们在化合物(IV)的合成中有用。
• [EN] PIPERIDINE AND PIPERAZINE DERIVATIVES AND THEIR USE IN TREATING VIRAL INFECTIONS AND CANCER<br/>[FR] DÉRIVÉS PIPÉRIDINE ET PIPÉRAZINE ET LEUR UTILISATION POUR TRAITER LES INFECTIONS VIRALES ET LE CANCER
  申请人：US HEALTH

  公开号：WO2015080949A1

  公开（公告）日：2015-06-04

  Disclosed are compounds of formula (I) (formula I),as antiviral agents, antineoplastic agents, pharmaceutical compositions comprising such compounds, and a method of use of these compounds, wherein X and Y are independently CH or N, o is 0, 1 or 2, and E is absent or is (CR13 R14 )m, NH, or S, F is absent or is (CR15 R16 )n, C=O, or -SO2 -, G is absent or is (CR17 CR18 )r, H is absent or is C=O, or -SO2 - and R1, Ar1, Ar2 are as defined in the specification. These compounds are antiviral agents and are contemplated in the treatment of viral infections, for example, hepatitis C, or are antineoplastic agents.

  揭示了化合物的结构式（I）（式I），作为抗病毒剂、抗肿瘤剂，包括这些化合物的药物组合物，以及这些化合物的使用方法，其中X和Y分别为CH或N，o为0、1或2，E不存在或为（CR13 R14）m、NH或S，F不存在或为（CR15 R16）n、C=O或-SO2-，G不存在或为（CR17 CR18）r，H不存在或为C=O或-SO2-，R1、Ar1、Ar2如规范中所定义。这些化合物是抗病毒剂，可用于治疗病毒感染，例如丙型肝炎，或作为抗肿瘤剂。
• Enantiomers of 1-[(4-chlorophenyl)phenylmethyl]-4-[(4-methylphenyl)
  申请人：U C B, S.A.

  公开号：US05478941A1

  公开（公告）日：1995-12-26

  Levorotatory and dextrorotatory enantiomers of 1-[(4-chlorophenyl)phenylmethyl]-4-[(4-methylphenyl)sulfonyl]piperazine of the formula ##STR1## their preparation and use for the preparation of substantially optically pure enantiomers of 1-[(4-chlorophenyl)phenylmethyl]piperazine, which are themselves valuable intermediate products for the preparation of optically active therapeutic compounds having a very high degree of optical purity.

  1-[(4-氯苯基)苯基甲基]-4-[(4-甲基苯基)磺酰基]哌嗪的左旋和右旋对映体，以及它们的制备和用于制备1-[(4-氯苯基)苯基甲基]哌嗪的基本光学纯度对映体，这些对映体本身是制备具有非常高光学纯度的光学活性治疗化合物的有价值中间产物。