ethyl 4-(p-fluorophenyl)-6-oxo-3-piperidinecarboxylate | 198640-82-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: ethyl 4-(p-fluorophenyl)-6-oxo-3-piperidinecarboxylate
• 英文别名: 3-Ethoxycarbonyl-4-(4'-fluorophenyl)piperidin-6-one；ethyl 4-(4-fluorophenyl)-6-oxopiperidine-3-carboxylate
• CAS: 198640-82-3
• 化学式: C₁₄H₁₆FNO₃
• 分子量: 265.284
• InChiKey: BZUOEEHWGFQIEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 4-(p-fluorophenyl)-6-oxo-3-piperidinecarboxylate 、 sodium ethanolate 、 在 乙酸乙酯 、 水 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以to obtain 50 mg of ethyl trans-4-(p-fluorophenyl)-6-oxo-3-piperidinecarboxylate的产率得到ethyl (3S,4R)-4-(4'-fluorophenyl)-6-oxopiperidin-3-carboxylate
  参考文献：
  名称：

  Process for producing piperidinecarbinols

  摘要：

  一种制备由通式（2）表示的哌啶基甲醇的方法，包括还原由通式（1）表示的化合物的反式异构体：其中R1是氢原子，低碳基或芳基烷基，R2是氢原子，低碳基，芳基或芳基烷基，X是氢原子，卤原子，烷基，芳基，芳基烷基，烷氧基，双烷基氨基基，烷硫基，芳基硫基或CmF2m+1—，其中m是1至20的整数。

  公开号：

  US06197960B1
• 作为产物：
  描述：

  diethyl 2-cyano-3-(4'-fluorophenyl)glutarate 以 甲醇 为溶剂， 生成 ethyl 4-(p-fluorophenyl)-6-oxo-3-piperidinecarboxylate
  参考文献：
  名称：

  Process for producing piperidinecarbinols

  摘要：

  一种制备通式（2）所示的哌啶基甲醇的方法，包括还原通式（1）所示的化合物的反式异构体：其中R1是氢原子、低碳基或芳基烷基，R2是氢原子、低碳基、芳基或芳基烷基，X是氢原子、卤素原子、烷基、芳基、芳基烷基、烷氧基、二烷基氨基基、烷硫基、芳硫基或CmF2m+1—，其中m是1至20的整数。

  公开号：

  US06197960B1

文献信息

• Process for preparing arylpiperidine carbinol intermediates and derivatives
  申请人：——

  公开号：US20010053862A1

  公开（公告）日：2001-12-20

  A process for the synthesis of arylpiperidine carbinol intermediates and derivatives is disclosed. A preferred process embodiment provides the synthesis of intermediate compounds of structural formula (I) and structural formula (II): 1 where X is halo, C 1 -C 10 alkoxy, C 1 -C 10 haloalkyl, or hydroxy; R 2 and R 3 are each C 1 -C 4 alkyl, and R 2 and R 3 are the same. The compound of structural formula (I) is made by condensing a corresponding cinnamonitrile with a corresponding diester malonate. The compound of structural formula (II) in the (±)-trans configuration is obtained by hydrogenating the compound of structural formula (I). The compounds of structural formula (I) and structural formula (II) are useful chemical intermediates for synthesizing 4-arylpiperidine-3-carbinols and their derivatives in (−)-trans configuration.

  本发明揭示了一种合成芳基哌啶羧醇中间体和衍生物的方法。首选的方法实施方式提供了结构式（I）和结构式（II）的中间化合物的合成：其中X是卤素，C1-C10烷氧基，C1-C10卤代烷基或羟基；R2和R3均为C1-C4烷基，并且R2和R3相同。结构式（I）的化合物是通过将相应的肉桂腈与相应的二酯丙二酸酯缩合而制得的。在（±）-反式构型下，通过氢化结构式（I）的化合物可获得结构式（II）的化合物。结构式（I）和结构式（II）的化合物是合成（-）-反式构型的4-芳基哌啶-3-羧醇及其衍生物的有用化学中间体。
• Process for preparing a piperidine derivative
  申请人：Sumika Fine Chemicals Co., Ltd.

  公开号：US20030144519A1

  公开（公告）日：2003-07-31

  A piperidine derivative, which can be used as an intermediate for pharmaceuticals such as paroxetine useful as antidepressants, represented by the general formula (I): 1 wherein R 1 is hydrogen atom, benzyloxycarbonyl group or tert-butoxycarbonyl group; R 2 is hydroxymethyl group, an alkylsulfonyloxymethyl group having an alkyl moiety of 1 to 2 carbon atoms, phenylsulfonyloxymethyl group which may have methyl group at the 4-position, (3,4-methylenedioxyphenyl)oxymethyl group, carboxyl group or —CO 2 R 7 group in which R 7 is an alkyl group having 1 to 5 carbon atoms, and Z is methylene group or carbonyl group, with proviso that, (A) when R 1 is benzyloxycarbonyl group or tert-butoxycarbonyl group, then R 2 is hydroxymethyl group, an alkylsulfonyloxymethyl group having an alkyl moiety of 1 to 2 carbon atoms, phenylsulfonyloxymethyl group which may have methyl group at the 4-position or (3,4-methylenedioxyphenyl)oxymethyl group, and Z is methylene group; or (B) when R 1 is hydrogen atom and Z is carbonyl group, then R 2 is carboxyl group or —CO 2 R 7 group (R 7 is as defined above); or (C) when R 1 is hydrogen atom and Z is methylene group, then R 2 is hydroxymethyl group

  一种哌啶衍生物，可用作如帕罗西汀等抗抑郁药物的中间体，由通式（I）表示：其中R1为氢原子，苄氧羰基基团或叔丁氧羰基基团；R2为羟甲基基团，具有1至2个碳原子的烷基磺酰氧甲基基团，可能在4位具有甲基基团的苯基磺酰氧甲基基团，（3,4-亚甲二氧基苯基）氧甲基基团，羧基或CO2R7基团，其中R7为具有1至5个碳原子的烷基基团，Z为亚甲基或羰基基团，但有附加条件，即（A）当R1为苄氧羰基基团或叔丁氧羰基基团时，R2为羟甲基基团，具有1至2个碳原子的烷基磺酰氧甲基基团，可能在4位具有甲基基团的苯基磺酰氧甲基基团或（3,4-亚甲二氧基苯基）氧甲基基团，而Z为亚甲基；或（B）当R1为氢原子且Z为羰基基团时，R2为羧基或CO2R7基团（其中R7如上所定义）；或（C）当R1为氢原子且Z为亚甲基时，R2为羟甲基基团。
• Piperidine derivative as intermediates for the preparation of paroxetine and process for their preparation
  申请人：SUMIKA FINE CHEMICALS Co., Ltd.

  公开号：EP0812827A1

  公开（公告）日：1997-12-17

  A piperidine derivative, which can be used as an intermediate for pharmaceuticals such as paroxetine useful as antidepressants, represented by the general formula (I): wherein R1 is hydrogen atom, benzyloxycarbonyl group or tert-butoxycarbonyl group; R2 is hydroxymethyl group, an alkylsulfonyloxymethyl group having an alkyl moiety of 1 to 2 carbon atoms, phenylsulfonyloxymethyl group which may have methyl group at the 4-position, (3,4-methylenedioxyphenyl)oxymethyl group, carboxyl group or -CO2R7 group in which R7 is an alkyl group having 1 to 5 carbon atoms, and Z is methylene group or carbonyl group, with proviso that, (A) when R1 is benzyloxycarbonyl group or tert-butoxycarbonyl group, then R2 is hydroxymethyl group, an alkylsulfonyloxymethyl group having an alkyl moiety of 1 to 2 carbon atoms, phenylsulfonyloxymethyl group which may have methyl group at the 4-position or (3,4-methylenedioxyphenyl)oxymethyl group, and Z is methylene group; or (B) when R1 is hydrogen atom and Z is carbonyl group, then R2 is carboxyl group or -CO2R7 group (R7 is as defined above); or (C) when R1 is hydrogen atom and Z is methylene group, then R2 is hydroxymethyl group. Also processes for the production of the intermediates are described.

  一种哌啶衍生物，可用作抗抑郁药帕罗西汀等药物的中间体，由通式(I)表示： 其中 R1 为氢原子、苄氧羰基或叔丁氧羰基；R2 是羟甲基、具有 1 至 2 个碳原子的烷基的烷磺酰氧基甲基、可在 4 位上具有甲基的苯磺酰氧基甲基、（3,4-亚甲基二氧苯基）氧基甲基、羧基或-CO2R7 基（其中 R7 是具有 1 至 5 个碳原子的烷基），Z 是亚甲基或羰基、但 (A) 当 R1 为苄氧羰基或叔丁氧羰基时，则 R2 为羟甲基、具有 1 至 2 个碳原子的烷基的烷基磺酰氧甲基、在 4 位可能具有甲基的苯基磺酰氧甲基或（3,4-亚甲基二氧苯基）氧甲基，且 Z 为亚甲基；或 (B) 当 R1 为氢原子且 Z 为羰基时，则 R2 为羧基或-CO2R7 基团（R7 如上定义）；或 (C) 当 R1 为氢原子且 Z 为亚甲基时，则 R2 为羟甲基。 此外，还介绍了中间体的生产工艺。
• Optical resolution of a piperidine derivative
  申请人：SUMIKA FINE CHEMICALS Co., Ltd.

  公开号：EP1384711A1

  公开（公告）日：2004-01-28

  The present invention relates to a method for preparing (3S,4R)-trans-4-(4-fluorophenyl)-3-hydroxymethylpiperidine represented by the formula (II): The method comprises the step of optically resolving (3SR,4RS)-trans-4-(4-fluorophenyl)-3-hydroxymethylpiperidine with o-chlorotartranilic acid as an optically active organic acid.

  本发明涉及一种制备式(II)代表的(3S,4R)-反式-4-(4-氟苯基)-3-羟甲基哌啶的方法： 该方法包括以下步骤：用邻氯酒石酸作为光学活性有机酸对(3SR,4RS)-反式-4-(4-氟苯基)-3-羟甲基哌啶进行光学解析。
• Process for drying paroxetine hydrochloride
  申请人：SUMIKA FINE CHEMICALS Co., Ltd.

  公开号：EP1384720A1

  公开（公告）日：2004-01-28

  The present invention relates to a method for drying paroxetine hydrochloride containing 8 to 15% by weight of isopropanol. The method comprises the steps of: (1) drying crystals of paroxetine hydrochloride containing 8 to 15% by weight of isopropanol obtained by the precipitation of crystals of paroxetine hydrochloride from an isopropanol solution of paroxetine hydrochloride, under reduced pressure at 70°C, and (2) drying the resulting paroxetine hydrochloride under a reduced pressure at a temperature of from 80° to 110°C to give paroxetine hydrochloride having an isopropanol content of 0.1 to 5% by weight.

  本发明涉及一种干燥盐酸帕罗西汀的方法，其中含有 8%至 15%（按重量计）的异丙醇。该方法包括以下步骤 (1) 在 70°C 的减压条件下，通过从盐酸帕罗西汀的异丙醇溶液中析出盐酸帕罗西汀结晶而得到的含 8 至 15%（重量）异丙醇的盐酸帕罗西汀结晶的干燥，以及 (2) 在 80° 至 110°C 的温度下减压干燥所得的盐酸帕罗西汀，得到异丙醇含量为 0.1%至 5%（按重量计）的盐酸帕罗西汀。