benzyl-(1-methyl-prop-2-ynyl)-amine; hydrochloride | 40591-14-8

• 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: benzyl-(1-methyl-prop-2-ynyl)-amine; hydrochloride
• 英文别名: Benzyl-(1-methyl-prop-2-inyl)-amin; Hydrochlorid；N-benzyl-N-methyl-propargyl-ammonium chloride；Benzyl(but-3-yn-2-yl)azanium;chloride；benzyl(but-3-yn-2-yl)azanium;chloride
• CAS: 40591-14-8
• 化学式: C₁₁H₁₃N*ClH
• 分子量: 195.692
• InChiKey: GCJQSQPHJXXYOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.22
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  16.6
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  苄基三甲基氯化铵 、 3-溴丙炔 、 N-甲基苄胺 在 sodium hydroxide 作用下， 以 水 、 苯 为溶剂， 生成 benzyl-(1-methyl-prop-2-ynyl)-amine; hydrochloride
  参考文献：
  名称：

  Process for the preparation of propargyl amines

  摘要：

  本发明涉及一种制备Formula I的丙炔基铵氯化物的新工艺，其中Formula I为##STR1##，通过碱性分解Formula II的1-异构体的d-酒石酸盐，然后在有机溶剂、碱和水的存在下，将Formula II的胺与Formula III的卤代烃X--CH.sub.2 --C.tbd.CH (III)反应，其中在Formula II和III中，n为1或0，X代表卤素。该工艺包括将Formula II的1-异构体的d-酒石酸盐在水悬浮液中与碱反应，将Formula II的碱通过不可溶于水的有机溶剂溶解，并在该相中与Formula III的卤代烃反应，然后在分离水层后，将Formula II和Formula IV的胺##STR3##在有机相中与有机酸或pH值为1.5-6的溶液（由无机酸和水组成）存在下反应，从而在形成的两相混合物中溶解Formula II的胺的盐在水层中，并选择性地从Formula IV的胺中分离出Formula II的胺，然后在分离相后向存在于有机相中的Formula IV的胺中加入氯化氢，从而沉淀Formula I的盐。Formula I化合物是已知的药物活性成分。本发明的优点在于它非常经济，并且能够在大规模生产中回收起始材料。

  公开号：

  US04564706A1

文献信息

• New process for the preparation of propargyl amines
  申请人：CHINOIN Gyogyszer és Vegyészeti Termékek Gyára RT.

  公开号：EP0099302A2

  公开（公告）日：1984-01-25

  The invention relates to a new process for the preparation of propargyl ammonium chlorides of the general Formula I by alkaline decomposition of the d-tartarate of the 1-isomer of an amine of the general Formula II and subsequent reaction of the amine of the general Formula II with a halide of the general Formula III in the presence of an organic solvent, alkali and water /in which general Formulae n is 1 or 0 and X stands for halogen/ which comprises reacting the d-tartarate of the 1-isomer of an amine of the general Formula II in aqueous suspension with an alkali, dissolving the base of the general Formula II, thus set free without isolation in a water non-miscible organic solvent and reacting the same in the said phase with a halide of the general Formula III, and thereafter - preferably after separating the aqueous layer - reacting the mixture which contains the amines of the general Formulae II and IV in the organic phase in the presence of water with an organic acid or a solution which has a pH value of 1.5-6 and consists of an inorganic acid and water, thus dissolving in the two-phase mixture formed the salt of the amine of the general Formula II in the aqueous layer and selectively separating the amine of the general Formula II from the amine of the general Formula IV, and thereafter adding after the separation of the phases hydrogen chloride to the amine of the general Formula IV being in the organic phase and thus precipitating the salt of the general Formula 1. The compounds of the general Formula I are known pharmaceutical active ingredients. The advantage of the process of the present invention that it is highly economical and enables the recovery of the starting materials on large scale production too.

  本发明涉及一种制备通式 I 丙炔基氯化铵的新工艺 通过通式 II 的胺的 1-异构体的 d-酒石酸盐的碱性分解 通式 II 的胺随后与通式 III 的卤化物反应 在有机溶剂、碱和水的存在下/其中通式为 n 为 1 或 0，且 X 代表卤素 其中包括在水悬浮液中将通式 II 的胺的 1-异构体的 d-酒石酸盐与碱反应，将通式 II 的碱溶解在不与水混溶的有机溶剂中，并在上述相中与通式 III 的卤化物反应，然后--最好在分离水层后--将含有通式 II 和 IV 的胺的混合物反应 在有机相中，在有水存在的情况下，与有机酸或 pH 值为 1.5-6 的由无机酸和水组成的溶液反应，从而在形成的两相混合物中溶解水层中的通式 II 的胺盐，并选择性地分离通式 II 的胺和通式 IV 的胺，然后在两相分离后向有机相中的通式 IV 的胺中加入氯化氢，从而沉淀出通式 1 的盐。 通式 I 的化合物是已知的药物活性成分。本发明工艺的优点是非常经济，而且可以在大规模生产中回收起始原料。
• EP0099302B1
  申请人：——

  公开号：EP0099302B1

  公开（公告）日：1986-10-01
• US4564706A
  申请人：——

  公开号：US4564706A

  公开（公告）日：1986-01-14
• Process for the preparation of propargyl amines
  申请人：Chinoin Gyogyszer es Vegyeszeti Termekek Gyara R.T.

  公开号：US04564706A1

  公开（公告）日：1986-01-14

  The invention relates to a new process for the preparation of propargyl ammonium chlorides of the Formula I ##STR1## by alkaline decomposition of the d-tartarate of the 1-isomer of an amine of the Formula II ##STR2## and subsequent reaction of the amine of the Formula II with a halide of the Formula III X--CH.sub.2 --C.tbd.CH (III) in the presence of an organic solvent, alkali and water in which in Formulae II and III respectively, n is 1 or 0 and X stands for halogen which comprises reacting the d-tartarate of the 1-isomer of an amine of the Formula II in aqueous suspension with an alkali, dissolving the base of the Formula II, thus set free without isolation in a water non-miscible organic solvent and reacting the same in the said phase with a halide of the Formula III, and thereafter--preferably after separating the aqueous layer--reacting the mixture which contains the amines of the Formulae II and IV ##STR3## in the organic phase in the presence of water with an organic acid or a solution which has a pH value of 1.5-6 and consists of an inorganic acid and water, thus dissolving in the two-phase mixture formed the salt of the amine of the Formula II in the aqueous layer and selectively separating the amine of the Formula II from the amine of the Formula IV, and thereafter adding after the separation of the phases hydrogen chloride to the amine of the Formula IV being in the organic phase and thus precipitating the salt of the Formula I. The compounds of Formula I are known pharmaceutical active ingredients. The advantage of the process of the present invention that it is highly economical and enables the recovery of the starting materials on large scale production too.

  本发明涉及一种制备Formula I的丙炔基铵氯化物的新工艺，其中Formula I为##STR1##，通过碱性分解Formula II的1-异构体的d-酒石酸盐，然后在有机溶剂、碱和水的存在下，将Formula II的胺与Formula III的卤代烃X--CH.sub.2 --C.tbd.CH (III)反应，其中在Formula II和III中，n为1或0，X代表卤素。该工艺包括将Formula II的1-异构体的d-酒石酸盐在水悬浮液中与碱反应，将Formula II的碱通过不可溶于水的有机溶剂溶解，并在该相中与Formula III的卤代烃反应，然后在分离水层后，将Formula II和Formula IV的胺##STR3##在有机相中与有机酸或pH值为1.5-6的溶液（由无机酸和水组成）存在下反应，从而在形成的两相混合物中溶解Formula II的胺的盐在水层中，并选择性地从Formula IV的胺中分离出Formula II的胺，然后在分离相后向存在于有机相中的Formula IV的胺中加入氯化氢，从而沉淀Formula I的盐。Formula I化合物是已知的药物活性成分。本发明的优点在于它非常经济，并且能够在大规模生产中回收起始材料。