N-[2-(benzenecarboximidoyl)-4-bromophenyl]-1-methylpiperidin-4-amine | 96110-81-5

• 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-[2-(benzenecarboximidoyl)-4-bromophenyl]-1-methylpiperidin-4-amine
• CAS: 96110-81-5
• 化学式: C₁₉H₂₂BrN₃
• 分子量: 372.308
• InChiKey: GRMHQPUDSPUQNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  39.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[2-(benzenecarboximidoyl)-4-bromophenyl]-1-methylpiperidin-4-amine 在 溶剂黄146 、 三氟乙酸 作用下， 以 乙醇 为溶剂， 反应 23.0h， 生成 7-bromo-1-(1-methylpiperidin-4-yl)-5-phenyl-3H-1,4-benzodiazepin-2-one
  参考文献：
  名称：

  1-Azacycloalkyl-1,4-benzodiazepin-2-ones with antianxiety-antidepressant actions

  摘要：

  A series of 1-azacycloalkyl-1,4-benzodiazepin-2-ones were synthesized from 1-azacycloalkyl-2-benzoylanilines and corresponding imines and then evaluated for their central nervous system activities. Pharmacological data showed that some of these compounds have potent antidepressant properties, as assessed by their antagonism of tetrabenzine (TBZ) induced ptosis and their inhibition of [3H]norepinephrine uptake into rat brain synaptosomes, as well as their moderate antianxiety properties of preventing of pentylenetetrazol (PTZ) convulsion, suppressing conflict behavior, and displacing potential for [3H]diazepam binding. Introduction of a halogen substituent at position 7 of the 1,4-benzodiazepine ring lengthened the anti-PTZ effects, although the peak effect was slightly reduced and clearly enhanced the anti-PTZ and anticonflict properties. Introduction of Cl to the ortho position of the phenyl ring at position 5 greatly reduced the antidepressant properties. The secondary amine function of the azacyclic ring at position 1 was essential for the production of the antidepressant properties. Of these new series, 7-fluoro-5-(2-fluorophenyl)-1,3-dihydro-1-(4-piperidinyl)-2H-1,4-benzodi azepin-2 -one has the potential to become a useful antidepressant drug with a moderate antianxiety property.

  DOI：

  10.1021/jm00383a003
• 作为产物：
  描述：

  N-甲基-4-哌啶酮 在 sodium hydroxide 、 sodium tetrahydroborate 、 molecular sieve 、 三氯化硼 作用下， 反应 25.0h， 生成 N-[2-(benzenecarboximidoyl)-4-bromophenyl]-1-methylpiperidin-4-amine
  参考文献：
  名称：

  Adachi, Makoto; Sasakura, Kazuyuki; Sugasawa, Tsutomu, Chemical and pharmaceutical bulletin, 1985, vol. 33, # 5, p. 1826 - 1835

  摘要：

  DOI：

文献信息

• Ortho-(mono-substituted amino)phenylimines and production thereof
  申请人：SHIONOGI & CO., LTD.

  公开号：EP0131921A2

  公开（公告）日：1985-01-23

  Novel ortho-(mono-substituted amino) phenylimines being intermediates to psychotropic drugs and other drugs are economically and industrially prepared by reacting anilines with nitriles in the presence of a boron tri-fluoride ether adduct and a halide-type Lewis acid, if necessary together with an organic base. Furthermore, the imines can be hydrolyzed with an acid to afford the corresponding ketones.

  新型正（单取代氨基）苯基亚胺是精神药物和其他药物的中间体，可通过苯胺与腈在三氟化硼醚加合物和卤化物型路易斯酸（必要时与有机碱一起）的存在下发生反应，以经济和工业化的方式制备。 此外，亚胺还可以用酸水解，得到相应的酮。
• ADACHI, MAKOTO;SASAKURA, KAZUYUKI;SUGASAWA, TSUTOMU
  作者：ADACHI, MAKOTO、SASAKURA, KAZUYUKI、SUGASAWA, TSUTOMU

  DOI：——

  日期：——
• ADACHI, MAKOTO;SASAKURA, KAZUYUKI;SUGASAWA, TSUTOMU, CHEM. AND PHARM. BULL., 1985, 33, N 5, 1826-1835
  作者：ADACHI, MAKOTO、SASAKURA, KAZUYUKI、SUGASAWA, TSUTOMU

  DOI：——

  日期：——
• US4831132A
  申请人：——

  公开号：US4831132A

  公开（公告）日：1989-05-16
• Adachi, Makoto; Sasakura, Kazuyuki; Sugasawa, Tsutomu, Chemical and pharmaceutical bulletin, 1985, vol. 33, # 5, p. 1826 - 1835
  作者：Adachi, Makoto、Sasakura, Kazuyuki、Sugasawa, Tsutomu

  DOI：——

  日期：——