[4-(Phenylamino)piperidin-4-yl]methanol

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: [4-(Phenylamino)piperidin-4-yl]methanol
• 英文别名: (4-anilinopiperidin-4-yl)methanol
• 化学式: C₁₂H₁₈N₂O
• mdl: MFCD09955354
• 分子量: 206.28
• InChiKey: KKNRLRCRJRGFJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44.3
• 氢给体数：
  3
• 氢受体数：
  3

文献信息

• Methods for the syntheses of alfentanil sufentanil and remifentanil
  申请人：——

  公开号：US20040138461A1

  公开（公告）日：2004-07-15

  Synthetic pathways are disclosed for synthesizing derivatives or analogs of fentanyl. Specifically set out are pathways for synthesizing alfentanil, sufentanil and remifentanil. The disclosed methods require fewer steps and produce a greater yield of product than methods reported in the prior art. The pathways to all these compounds begin with a common pathway of condensing a piperidone with a primary amine so as to form a 4-amino carboxyamino-piperidine, wherein N of said piperidone is a —N—COO—(CH 2 ) n CH 3 , alkylating an N of said primary amine which was condensed with said piperidone thereby producing an N-alkyl-anilide, and hydrolyzing said —COO—(CH 2 ) n CH 3? group of said 4-amino-4-carboxyamino-piperidine following the condensation reaction so as to form a piperidine hydrolysis product. This product can then be convened to remifentanil in a 4 step reaction. Also, this hydrolysis product can be treated with a hydride to yield a 4-hydroxymthyl-piperidine which can be converted to alfentanil in 3 further steps, to sufentanil in 3 more steps, or to a variety of remifentanil analogs in two steps.

  本文披露了合成芬太尼衍生物或类似物的合成途径。具体介绍了合成阿芬太尼、舒芬太尼和瑞芬太尼的途径。所披露的方法需要的步骤更少，产物收率比先前报道的方法更高。所有这些化合物的途径都始于将哌啶酮与一种一级胺缩合，从而形成4-氨基羧氨基哌啶，其中所述哌啶酮的N为—N—COO—(CH2)nCH3，烷基化所述与所述哌啶酮缩合的所述一级胺的N，从而产生一种N-烷基酰胺，然后水解所述缩合反应的4-氨基-4-羧氨基哌啶中的所述—COO—( )nCH3?基团，从而形成哌啶水解产物。然后，可以通过4步反应将该产物转化为瑞芬太尼。此外，该水解产物可以用氢化物处理，产生4-羟甲基哌啶，可以通过3个进一步的步骤将其转化为阿芬太尼，通过3个更多的步骤将其转化为舒芬太尼，或者通过两个步骤将其转化为各种瑞芬太尼类似物。
• [EN] NEW METHODS FOR THE SYNTHESES OF ALFENTANIL, SUFENTANIL AND REMIFENTANIL<br/>[FR] NOUVELLES METHODES DE SYNTHESE D'ALFENTANIL, DE SUFENTANIL ET DE REMIFENTANIL
  申请人：MALLINCKRODT INC

  公开号：WO2001040184A2

  公开（公告）日：2001-06-07

  Synthetic pathways are disclosed for synthesizing derivatives or analogs of fentanyl. Specifically set out are pathways for synthesizing alfentanil, sufentanil and remifentanil. The disclosed methods require fewer steps and produce a greater yield of product than methods reported in the prior art. The pathways to all these compounds begin with a common pathway of condensing a piperidone with a primary amine so as to form a 4-amino-4-carboxyamino-piperidine, wherein N of said piperidone is a -N-COO-(CH2)nCH3, alkylating an N of said primary amine which was condensed with said piperidone thereby producing an N-alkyl-anilide, and hydrolyzing said -COO-(CH2)nCH3 group of said 4-amino-4-carboxyamino-piperidine following the condensation reaction so as to form a piperidine hydrolysis product. This product can then be converted to remifentanil in a 4 step reaction. Also, this hydrolysis product can be treated with a hydride to yield a 4-hydroxymethyl-piperidine which can be converted to alfentanil in 3 further steps, to sufentanil in 3 more steps, or to a variety of remifentanil analogs in two steps.

  揭示了合成芬太尼衍生物或类似物的合成途径。具体列出了合成阿芬太尼、舒芬太尼和瑞芬太尼的途径。所揭示的方法需要较少的步骤，并且产量比先前报道的方法更高。所有这些化合物的途径都始于将哌啶酮与一种一级胺缩合以形成4-氨基-4-羧基氨基哌啶的共同途径，其中所述哌啶酮的N为-N-COO-（CH2）nCH3，烷基化所述与所述哌啶酮缩合的所述一级胺的N，从而产生一种N-烷基酰胺，以及在缩合反应后水解所述4-氨基-4-羧基氨基哌啶的所述-COO-（ ）nCH3基团，从而形成哌啶水解产物。然后，该产物可以通过4步反应转化为瑞芬太尼。此外，可以用还原剂处理该水解产物以产生4-羟甲基哌啶，然后通过3个进一步的步骤将其转化为阿芬太尼，通过另外3个步骤将其转化为舒芬太尼，或通过2个步骤将其转化为各种瑞芬太尼类似物。
• New methods for the synthesis of alfentanil, sufentanil, and remifentanil
  申请人：Mathew Jacob

  公开号：US20060149071A1

  公开（公告）日：2006-07-06

  Synthetic pathways are disclosed for synthesizing derivatives or analogs of fentanyl. Specifically set out are pathways for synthesizing alfentanil, sufentanil and remifentanil. The disclosed methods require fewer steps and produce a greater yield of product than methods reported in the prior art.

  本文披露了合成芬太尼衍生物或类似物的合成途径。具体列出了合成阿芬太尼、舒芬太尼和瑞芬太尼的途径。披露的方法所需步骤较少，产量比先前报道的方法更高。
• METHODS FOR THE SYNTHESES OF ALFENTANIL, SUFENTANIL AND REMIFENTANIL
  申请人：MALLINCKRODT INC.

  公开号：EP1246801B1

  公开（公告）日：2006-09-20
• US7074935B2
  申请人：——

  公开号：US7074935B2

  公开（公告）日：2006-07-11