1'-Phenyl-N-methyl-2-piperidinemethanol | 54364-79-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1'-Phenyl-N-methyl-2-piperidinemethanol
• 英文别名: (1-methyl-piperidin-2-yl)-phenyl-methanol；(1S)-[(2S)-(1-methylpiperidin-2-yl)]phenylmethanol；N-methyl-2-[(1-phenyl)(1-hydroxy)methyl]piperidine；2-(α-hydroxybenzyl)-N-methylpiperidine；(1-methyl-2-piperidyl)-1-phenylmethanol；Phenyl--carbinol；2-Piperidinemethanol,1-methyl-a-phenyl-；(1-methylpiperidin-2-yl)-phenylmethanol
• CAS: 54364-79-3
• 化学式: C₁₃H₁₉NO
• 分子量: 205.3
• InChiKey: JGAYLCZXGQAXQC-UHFFFAOYSA-N

物化性质

• 熔点：
  61-62 °C
• 沸点：
  140-143 °C(Press: 5.5 Torr)
• 密度：
  1.057±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1'-Phenyl-N-methyl-2-piperidinemethanol 在 三乙胺 作用下， 生成 N-methyl-1-(1-methylpiperidin-2-yl)-1-phenylmethanamine
  参考文献：
  名称：

  Syntheses of 1,2-diamino and 1,2-aminoalcohol derivatives in the piperidine and pyrrolidine series as anti-amnesic agents

  摘要：

  Tacrine, one of the drugs available for Alzheimer's disease based on the cholinergic approach, suffers from considerable toxicity. Many analogues of tacrine has been prepared which retain the pharmacologically rich aminopyridine or aminoquinoline motifs. The current research is a continuation of our efforts in the area of 11-aminobenzoquinolizidines (4) and 10-aminobenzoindolizidines (5) (cf. ref 9). A serendipitous discovery led us to the biologically active open chain analogue 9, and we proceeded to elaborate on this molecule. Overall, the compounds we prepared were poor inhibitors of acetylcholinesterase as compared to tacrine. The single exception was compound 20 which exhibited an effect comparable to that of tacrine, but only at a dose in the order of 10(-3) M. However, despite the poor acetylcholinesterase inhibition by 9, this compound was found to be an effective antiamnesic agent. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00079-6
• 作为产物：
  描述：

  (1-Methylpyridin-1-ium-2-yl)-phenylmethanone;trifluoromethanesulfonate 在 Rh on carbon 氢气 作用下， 生成 1'-Phenyl-N-methyl-2-piperidinemethanol
  参考文献：
  名称：

  Syntheses of 1,2-diamino and 1,2-aminoalcohol derivatives in the piperidine and pyrrolidine series as anti-amnesic agents

  摘要：

  Tacrine, one of the drugs available for Alzheimer's disease based on the cholinergic approach, suffers from considerable toxicity. Many analogues of tacrine has been prepared which retain the pharmacologically rich aminopyridine or aminoquinoline motifs. The current research is a continuation of our efforts in the area of 11-aminobenzoquinolizidines (4) and 10-aminobenzoindolizidines (5) (cf. ref 9). A serendipitous discovery led us to the biologically active open chain analogue 9, and we proceeded to elaborate on this molecule. Overall, the compounds we prepared were poor inhibitors of acetylcholinesterase as compared to tacrine. The single exception was compound 20 which exhibited an effect comparable to that of tacrine, but only at a dose in the order of 10(-3) M. However, despite the poor acetylcholinesterase inhibition by 9, this compound was found to be an effective antiamnesic agent. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00079-6

文献信息

• Indole derivatives
  申请人：Nisshin Flour Milling Co., Ltd.

  公开号：US05124324A1

  公开（公告）日：1992-06-23

  Disclosed are compounds of formula I ##STR1## wherein R.sub.1 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, benzyl or an indolyl carbonyl group, R.sub.2 is a saturated or unsaturated 5- or 8-membered heterocyclic group containing as a hetero atom one or more nitrogen atoms, the heterocyclic group is optionally substituted at an N or C atom by a C.sub.1 -C.sub.6 alkyl or aralkyl group, n is an integer of 1 to 5 and one or more hydrogen atoms, in an alkylene chain --(CH.sub.2).sub.n -- are optionally substituted by a C.sub.1 -C.sub.6 alkyl, phenyl and/or hydroxyl group, physiologically acceptable salts and quaternary ammonium salts thereof. The compounds are selective antagonists of 5-HT.sub.3 receptors and are useful in the treatment of psychotic disorders, neurotic diseases, gastric stasis symptoms, gastrointestinal disorders, nausea and vomiting.

  公开的是I式化合物，其中R.sub.1是氢原子、C.sub.1 -C.sub.6烷基、苄基或吲哚基酰基，R.sub.2是含有一个或多个氮原子的饱和或不饱和5-或8-成员杂环基团，该杂环基团在N或C原子上可以被C.sub.1 -C.sub.6烷基或芳基烷基取代，n是1到5的整数和一个或多个氢原子，在烷基链--(CH.sub.2).sub.n --中的一个或多个氢原子可以被C.sub.1 -C.sub.6烷基、苯基和/或羟基取代，其生理学上可接受的盐和季铵盐。这些化合物是5-HT.sub.3受体的选择性拮抗剂，可用于治疗精神障碍、神经病、胃排空延迟症状、胃肠道疾病、恶心和呕吐。
• (Amidomethyl)nitrogen heterocyclic analgesics
  申请人：The Du Pont Merck Pharmaceutical Company

  公开号：US05254569A1

  公开（公告）日：1993-10-19

  This invention relates to (amidomethyl)nitrogen heterocyclic and pyrrolidine compounds, pharmaceutical compositions containing them, methods of using such compounds and processes for making such compounds.

  本发明涉及（酰胺甲基）氮杂环和吡咯烷化合物，包含它们的制药组合物，使用这种化合物的方法以及制造这种化合物的过程。
• N-[PHENYL(PIPERIDIN-2-YL)METHYL]BENZAMIDE DERIVATIVES, PREPARATION THEREOF, AND USE THEREOF IN THERAPY
  申请人：DARGAZANLI Gihad

  公开号：US20070155789A1

  公开（公告）日：2007-07-05

  This invention discloses and claims a compound of general formula (I) in which R 1 represents either a hydrogen atom, or an optionally substituted alkyl group, or a cycloalkylalkyl group, or an optionally substituted phenylalkyl group, or an alkenyl group, X represents a hydrogen atom or one or more substituents chosen from halogen atoms and trifluoromethyl, alkyl and alkoxy groups, R 2 represents one or more substituents chosen from halogen atoms, optionally substituted alkoxy and optionally substituted amino. The compounds of this invention exhibit therapeutic utility.

  本发明揭示并声明了一种通式（I）的化合物，其中R1代表氢原子，或者是一个可选取代的烷基基团，或者是一个环烷基烷基团，或者是一个可选取代的苯基烷基团，或者是烯基基团，X代表氢原子或一个或多个取代基，所选取代基来自卤素原子和三氟甲基，烷基和烷氧基，R2代表一个或多个取代基，所选取代基来自卤素原子，可选取代的烷氧基和可选取代的氨基。本发明的化合物具有治疗用途。
• Use of N-[Phenyl(piperidin-2-yl)methyl]benzamide derivatives in therapy
  申请人：DARGAZANLI Gihad

  公开号：US20070197601A1

  公开（公告）日：2007-08-23

  The present invention discloses and claims therapeutic use of a series of compounds of general formula (I) in which A, X and R 2 are as described herein. Specifically, the compounds of formula (I) exhibit a particular activity as specific inhibitors of the glycine transporters glyt1 and/or glty2.

  本发明揭示和声明了一系列通式(I)的化合物的治疗用途，其中A、X和R2如本文所述。具体而言，通式(I)的化合物表现出一种特定的活性，作为甘氨酸转运体glyt1和/或glyt2的特异性抑制剂。
• DERIVATIVES OF N-PHENYL(PIPERIDINE-2-YL) METHYL BENZAMIDE PREPARATION METHOD THEREOF AND APPLICATIONS OF SAME IN THERAPEUTICS
  申请人：DARGAZANLI Gihad

  公开号：US20100234424A1

  公开（公告）日：2010-09-16

  Compounds of formula (I) as defined herein: are useful for treating behavioral disorders associated with dementia, psychoses, in particular schizophrenia (deficient form and productive form) and acute or chronic extrapyramidal symptoms induced by neuroleptics; for the treatment of various forms of anxiety, panic attacks, phobias, and compulsive obsessive disorders; for treating various forms of depression, including psychotic depression; for treating disorders caused by alcohol abuse or weaning from alcohol, sexual behavior disorders, eating disorders and for treating migraine. Moreover, the compounds of the invention may be used for treating painful muscle contracture in rheumatology and in acute spinal pathology; for treating spastic contractures of medullary or cerebral origin; for the symptomatic treatment of acute and subacute pain of light to moderate intensity; for treating intense and/or chronic pain, neurogenic pain and intractable pain; for treating Parkinson's disease and Parkinson-like symptoms of neurodegenerative origin or induced by neuroleptics; for treating partial primary and secondary generalized epilepsy of simple or complex symptomology, mixed forms and other epileptic syndromes in addition to another antiepileptic treatment, or in monotherapy, for the treatment of sleep apnea, and for neuroprotection.

  本文中定义的化合物（I）的配方，可用于治疗与痴呆症、精神病有关的行为障碍，特别是精神分裂症（缺陷型和产生型）和由神经阻滞剂引起的急性或慢性锥体外症状；用于治疗各种形式的焦虑、惊恐发作、恐惧症和强迫性障碍；用于治疗各种形式的抑郁症，包括精神病性抑郁症；用于治疗由酒精滥用或戒酒引起的障碍、性行为障碍、进食障碍以及治疗偏头痛。此外，该发明的化合物可用于治疗风湿病中的疼痛性肌肉挛缩和急性脊柱病理学；用于治疗髓性或脑性起源的痉挛性挛缩；用于轻至中度强度的急性和亚急性疼痛的症状性治疗；用于治疗剧烈和/或慢性疼痛、神经性疼痛和难治性疼痛；用于治疗帕金森病和神经退行性起源或由神经阻滞剂引起的帕金森样症状；用于治疗简单或复杂症状学、混合形式和其他癫痫综合征的部分原发性和继发性广泛性癫痫，除另一种抗癫痫治疗外，或单独治疗，用于治疗睡眠呼吸暂停和神经保护作用。